Category: 22348-32-9

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22348-32-9,(R)-Diphenyl(pyrrolidin-2-yl)methanol,as a common compound, the synthetic route is as follows.

To (S)-diphenylprolinol (4.00 g, 15.8 mmol, 1.00 equiv) in CH2-Cl2 (40 mL) was added imidazole (3.22 g, 47.4 mmol, 3.00 equiv)at 0 C. TMSCl (5.00 mL, 39.5 mmol, 2.50 equiv) was added dropwiseand the reaction was stirred for 12 h at rt. MTBE (100 mL)was added to the reaction and the mixture was filtered. Theorganic phase was washed with H2O (50 mL) and saturated aqueousNaCl (2 50 mL), dried over MgSO4, filtered and concentratedunder reduced pressure to a colorless oil 11 (5.00 g, 15.3 mmol,97%). 1H NMR (400 MHz, CDCl3) d 7.54-7.46 (m, 2H), 7.42-7.36(m, 2H), 7.35-7.20 (m, 6H), 4.07 (t, J = 7.4 Hz, 1H), 2.98-2.75 (m,2H), 1.84-1.72 (m, 1H), 1.68-1.55 (m, 3H), 1.48-1.37 (m, 1H),0.06 (s, 9H) ppm. 13C NMR (101 MHz, CDCl3) d 146.83, 145.78,128.44, 127.61, 127.57, 127.53, 126.90, 126.73, 83.17, 65.42,47.16, 27.51, 25.06, 2.20 ppm. HR-MS (ESI): calculated for (C20H28-NOSi) [M+H]+: 326.1935, found: 326.1937.

22348-32-9, As the paragraph descriping shows that 22348-32-9 is playing an increasingly important role.

Reference：
Article; Murar, Claudia E.; Harmand, Thibault J.; Bode, Jeffrey W.; Bioorganic and Medicinal Chemistry; vol. 25; 18; (2017); p. 4996 – 5001;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

22348-32-9, (R)-Diphenyl(pyrrolidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3A. Preparation of TMS-prolinolTo a mixture of prolinol (10.0 g, 39.5 mmol) and imidazole (4.57 g, 67.1 mmol) in THF (100 mL) was added chlorotrimethylsilane (5.57 g, 51.3 mmol) over 15 min while maintaining the batch temperature below 30 0C. The resulting slurry was aged at 50 0C for 3-5 h. The reaction mixture was cooled to ambient tempearture and quenched by addition of MTBE (50 mL) and 15% aq NaCl (100 mL). The organic layer was washed with 15% aq NaCl (50 mL). The solution was azeotropically dried at the constant volume by feeding THF.HPLC MethodColumn: Ascentis Express Cl 8 (100×4.6mm, 2.7um)Column temperature: 45 0CFlow rate: 1.5 ml/minDetection: UV at 210nmGradient:Time(min) 0.1% H^PO4 (0A) MeCN (0A)0 95 51 95 512 10 90Retention times (minutes): prolinol (4.8 min); TMS prolinol (7.3 min), 22348-32-9

The synthetic route of 22348-32-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP &; DOHME CORP.; XU, Feng; DESMOND, Richard; HOERRNER, R. Scott; HUMPHREY, Guy, R.; ITOH, Tetsuji; JOURNET, Michel; YOSHIKAWA, Naoki; ZACUTO, Michael, J.; WO2010/144293; (2010); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22348-32-9,(R)-Diphenyl(pyrrolidin-2-yl)methanol,as a common compound, the synthetic route is as follows.

A solution of (S)-(-)-alpha,alpha-diphenyl-2-pyrrolidinemethanol (240 mg, 0.97 mmol) and 2 M Borane-Dimethylsulfide complex (in THF, 3.4 mL, 6.8 mmol) in dry THF (50 mL) was stirred at rt under N2 for 16 h. A solution of 5-(4-Fluoro-phenyl)-3-oxo-pentanoic acid ethyl ester (2.03 g, 8.57 mmol) in dry THF (20 mL) was then added dropwise at rt over a period of 1 h. The resultant clear solution was stirred at rt for another 35 min and was then cooled to 0 C. in an ice bath. The reaction was quenched by the addition of EtOH (40 mL) and was concentrated under reduced pressure. The residue was taken up with EtOAc (100 mL) and washed successively with H2O (50 mL), 5% NaHCO3 (50 mL), brine (50 mL), and then dried over Na2SO4. Removal of the solvent afforded an oil, which was purified by flush column chromatography on silica gel. The intermediate S-5-(4-Fluoro-phenyl)-3-hydroxy-pentanoic acid ethyl ester was obtained as a colorless oil (1.33 g, 65%). 1H NMR (300 MHz, CDCl3) delta1.25 (t, 3H, J=7), 1.6-1.9 (m, 2H), 2.35-2.50 (m, 2H), 2.60-2.85 (m, 2H), 3.1 (d, 1H, J=5), 3.95-4.05 (m, 1H), 4.1-4.25 (m, 2H), 6.9-7.0 (m, 2H), 7.05-7.2 (m, 2H). ESMS calcd (C13H17FO3): 240.1; found: 241.1 (M+H)+.

22348-32-9, 22348-32-9 (R)-Diphenyl(pyrrolidin-2-yl)methanol 7045371, acatalyst-ligand compound, is more and more widely used in various fields.

Reference：
Patent; Chen, Shoujun; Sun, Lijun; McCleary, Joel; US2003/60633; (2003); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22348-32-9,(R)-Diphenyl(pyrrolidin-2-yl)methanol,as a common compound, the synthetic route is as follows.

To (S)-diphenylprolinol (4.00 g, 15.8 mmol, 1.00 equiv) in CH2-Cl2 (40 mL) was added imidazole (3.22 g, 47.4 mmol, 3.00 equiv)at 0 C. TMSCl (5.00 mL, 39.5 mmol, 2.50 equiv) was added dropwiseand the reaction was stirred for 12 h at rt. MTBE (100 mL)was added to the reaction and the mixture was filtered. Theorganic phase was washed with H2O (50 mL) and saturated aqueousNaCl (2 50 mL), dried over MgSO4, filtered and concentratedunder reduced pressure to a colorless oil 11 (5.00 g, 15.3 mmol,97%). 1H NMR (400 MHz, CDCl3) d 7.54-7.46 (m, 2H), 7.42-7.36(m, 2H), 7.35-7.20 (m, 6H), 4.07 (t, J = 7.4 Hz, 1H), 2.98-2.75 (m,2H), 1.84-1.72 (m, 1H), 1.68-1.55 (m, 3H), 1.48-1.37 (m, 1H),0.06 (s, 9H) ppm. 13C NMR (101 MHz, CDCl3) d 146.83, 145.78,128.44, 127.61, 127.57, 127.53, 126.90, 126.73, 83.17, 65.42,47.16, 27.51, 25.06, 2.20 ppm. HR-MS (ESI): calculated for (C20H28-NOSi) [M+H]+: 326.1935, found: 326.1937.

22348-32-9, As the paragraph descriping shows that 22348-32-9 is playing an increasingly important role.

Reference：
Article; Murar, Claudia E.; Harmand, Thibault J.; Bode, Jeffrey W.; Bioorganic and Medicinal Chemistry; vol. 25; 18; (2017); p. 4996 – 5001;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

22348-32-9, (R)-Diphenyl(pyrrolidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3A. Preparation of TMS-prolinolTo a mixture of prolinol (10.0 g, 39.5 mmol) and imidazole (4.57 g, 67.1 mmol) in THF (100 mL) was added chlorotrimethylsilane (5.57 g, 51.3 mmol) over 15 min while maintaining the batch temperature below 30 0C. The resulting slurry was aged at 50 0C for 3-5 h. The reaction mixture was cooled to ambient tempearture and quenched by addition of MTBE (50 mL) and 15% aq NaCl (100 mL). The organic layer was washed with 15% aq NaCl (50 mL). The solution was azeotropically dried at the constant volume by feeding THF.HPLC MethodColumn: Ascentis Express Cl 8 (100×4.6mm, 2.7um)Column temperature: 45 0CFlow rate: 1.5 ml/minDetection: UV at 210nmGradient:Time(min) 0.1% H^PO4 (0A) MeCN (0A)0 95 51 95 512 10 90Retention times (minutes): prolinol (4.8 min); TMS prolinol (7.3 min), 22348-32-9

The synthetic route of 22348-32-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP &; DOHME CORP.; XU, Feng; DESMOND, Richard; HOERRNER, R. Scott; HUMPHREY, Guy, R.; ITOH, Tetsuji; JOURNET, Michel; YOSHIKAWA, Naoki; ZACUTO, Michael, J.; WO2010/144293; (2010); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22348-32-9,(R)-Diphenyl(pyrrolidin-2-yl)methanol,as a common compound, the synthetic route is as follows.

To (S)-diphenylprolinol (4.00 g, 15.8 mmol, 1.00 equiv) in CH2-Cl2 (40 mL) was added imidazole (3.22 g, 47.4 mmol, 3.00 equiv)at 0 C. TMSCl (5.00 mL, 39.5 mmol, 2.50 equiv) was added dropwiseand the reaction was stirred for 12 h at rt. MTBE (100 mL)was added to the reaction and the mixture was filtered. Theorganic phase was washed with H2O (50 mL) and saturated aqueousNaCl (2 50 mL), dried over MgSO4, filtered and concentratedunder reduced pressure to a colorless oil 11 (5.00 g, 15.3 mmol,97%). 1H NMR (400 MHz, CDCl3) d 7.54-7.46 (m, 2H), 7.42-7.36(m, 2H), 7.35-7.20 (m, 6H), 4.07 (t, J = 7.4 Hz, 1H), 2.98-2.75 (m,2H), 1.84-1.72 (m, 1H), 1.68-1.55 (m, 3H), 1.48-1.37 (m, 1H),0.06 (s, 9H) ppm. 13C NMR (101 MHz, CDCl3) d 146.83, 145.78,128.44, 127.61, 127.57, 127.53, 126.90, 126.73, 83.17, 65.42,47.16, 27.51, 25.06, 2.20 ppm. HR-MS (ESI): calculated for (C20H28-NOSi) [M+H]+: 326.1935, found: 326.1937.

22348-32-9, As the paragraph descriping shows that 22348-32-9 is playing an increasingly important role.

Reference：
Article; Murar, Claudia E.; Harmand, Thibault J.; Bode, Jeffrey W.; Bioorganic and Medicinal Chemistry; vol. 25; 18; (2017); p. 4996 – 5001;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

22348-32-9, (R)-Diphenyl(pyrrolidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3A. Preparation of TMS-prolinolTo a mixture of prolinol (10.0 g, 39.5 mmol) and imidazole (4.57 g, 67.1 mmol) in THF (100 mL) was added chlorotrimethylsilane (5.57 g, 51.3 mmol) over 15 min while maintaining the batch temperature below 30 0C. The resulting slurry was aged at 50 0C for 3-5 h. The reaction mixture was cooled to ambient tempearture and quenched by addition of MTBE (50 mL) and 15% aq NaCl (100 mL). The organic layer was washed with 15% aq NaCl (50 mL). The solution was azeotropically dried at the constant volume by feeding THF.HPLC MethodColumn: Ascentis Express Cl 8 (100×4.6mm, 2.7um)Column temperature: 45 0CFlow rate: 1.5 ml/minDetection: UV at 210nmGradient:Time(min) 0.1% H^PO4 (0A) MeCN (0A)0 95 51 95 512 10 90Retention times (minutes): prolinol (4.8 min); TMS prolinol (7.3 min), 22348-32-9

The synthetic route of 22348-32-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP &; DOHME CORP.; XU, Feng; DESMOND, Richard; HOERRNER, R. Scott; HUMPHREY, Guy, R.; ITOH, Tetsuji; JOURNET, Michel; YOSHIKAWA, Naoki; ZACUTO, Michael, J.; WO2010/144293; (2010); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22348-32-9,(R)-Diphenyl(pyrrolidin-2-yl)methanol,as a common compound, the synthetic route is as follows.

To (S)-diphenylprolinol (4.00 g, 15.8 mmol, 1.00 equiv) in CH2-Cl2 (40 mL) was added imidazole (3.22 g, 47.4 mmol, 3.00 equiv)at 0 C. TMSCl (5.00 mL, 39.5 mmol, 2.50 equiv) was added dropwiseand the reaction was stirred for 12 h at rt. MTBE (100 mL)was added to the reaction and the mixture was filtered. Theorganic phase was washed with H2O (50 mL) and saturated aqueousNaCl (2 50 mL), dried over MgSO4, filtered and concentratedunder reduced pressure to a colorless oil 11 (5.00 g, 15.3 mmol,97%). 1H NMR (400 MHz, CDCl3) d 7.54-7.46 (m, 2H), 7.42-7.36(m, 2H), 7.35-7.20 (m, 6H), 4.07 (t, J = 7.4 Hz, 1H), 2.98-2.75 (m,2H), 1.84-1.72 (m, 1H), 1.68-1.55 (m, 3H), 1.48-1.37 (m, 1H),0.06 (s, 9H) ppm. 13C NMR (101 MHz, CDCl3) d 146.83, 145.78,128.44, 127.61, 127.57, 127.53, 126.90, 126.73, 83.17, 65.42,47.16, 27.51, 25.06, 2.20 ppm. HR-MS (ESI): calculated for (C20H28-NOSi) [M+H]+: 326.1935, found: 326.1937., 22348-32-9

As the paragraph descriping shows that 22348-32-9 is playing an increasingly important role.

Reference：
Article; Murar, Claudia E.; Harmand, Thibault J.; Bode, Jeffrey W.; Bioorganic and Medicinal Chemistry; vol. 25; 18; (2017); p. 4996 – 5001;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

22348-32-9, (R)-Diphenyl(pyrrolidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3A. Preparation of TMS-prolinolTo a mixture of prolinol (10.0 g, 39.5 mmol) and imidazole (4.57 g, 67.1 mmol) in THF (100 mL) was added chlorotrimethylsilane (5.57 g, 51.3 mmol) over 15 min while maintaining the batch temperature below 30 0C. The resulting slurry was aged at 50 0C for 3-5 h. The reaction mixture was cooled to ambient tempearture and quenched by addition of MTBE (50 mL) and 15% aq NaCl (100 mL). The organic layer was washed with 15% aq NaCl (50 mL). The solution was azeotropically dried at the constant volume by feeding THF.HPLC MethodColumn: Ascentis Express Cl 8 (100×4.6mm, 2.7um)Column temperature: 45 0CFlow rate: 1.5 ml/minDetection: UV at 210nmGradient:Time(min) 0.1% H^PO4 (0A) MeCN (0A)0 95 51 95 512 10 90Retention times (minutes): prolinol (4.8 min); TMS prolinol (7.3 min)

22348-32-9, The synthetic route of 22348-32-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP &; DOHME CORP.; XU, Feng; DESMOND, Richard; HOERRNER, R. Scott; HUMPHREY, Guy, R.; ITOH, Tetsuji; JOURNET, Michel; YOSHIKAWA, Naoki; ZACUTO, Michael, J.; WO2010/144293; (2010); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22348-32-9,(R)-Diphenyl(pyrrolidin-2-yl)methanol,as a common compound, the synthetic route is as follows.

A solution of (S)-(-)-alpha,alpha-diphenyl-2-pyrrolidinemethanol (240 mg, 0.97 mmol) and 2 M Borane-Dimethylsulfide complex (in THF, 3.4 mL, 6.8 mmol) in dry THF (50 mL) was stirred at rt under N2 for 16 h. A solution of 5-(4-Fluoro-phenyl)-3-oxo-pentanoic acid ethyl ester (2.03 g, 8.57 mmol) in dry THF (20 mL) was then added dropwise at rt over a period of 1 h. The resultant clear solution was stirred at rt for another 35 min and was then cooled to 0 C. in an ice bath. The reaction was quenched by the addition of EtOH (40 mL) and was concentrated under reduced pressure. The residue was taken up with EtOAc (100 mL) and washed successively with H2O (50 mL), 5% NaHCO3 (50 mL), brine (50 mL), and then dried over Na2SO4. Removal of the solvent afforded an oil, which was purified by flush column chromatography on silica gel. The intermediate S-5-(4-Fluoro-phenyl)-3-hydroxy-pentanoic acid ethyl ester was obtained as a colorless oil (1.33 g, 65%). 1H NMR (300 MHz, CDCl3) delta1.25 (t, 3H, J=7), 1.6-1.9 (m, 2H), 2.35-2.50 (m, 2H), 2.60-2.85 (m, 2H), 3.1 (d, 1H, J=5), 3.95-4.05 (m, 1H), 4.1-4.25 (m, 2H), 6.9-7.0 (m, 2H), 7.05-7.2 (m, 2H). ESMS calcd (C13H17FO3): 240.1; found: 241.1 (M+H)+.

22348-32-9, 22348-32-9 (R)-Diphenyl(pyrrolidin-2-yl)methanol 7045371, acatalyst-ligand compound, is more and more widely used in various fields.

Reference：
Patent; Chen, Shoujun; Sun, Lijun; McCleary, Joel; US2003/60633; (2003); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI