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