Analyzing the synthesis route of 294-90-6

The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

294-90-6, 1,4,7,10-Tetraazacyclododecane is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-(tert-Butoxycarbonyloxy)succinimide (2.50 g, 11.62 mmol) inchloroform (30 mL) was added dropwise into the solution of1,4,7,10-tetraazacyclododecane (1.00 g, 5.80 mmol) in CHCl3(50 mL) during 7 h. The reaction mixture was stirred 24 h at roomtemperature and the solvent was removed under reduced pressure. The residue was suspended in aqueous NaOH (3 M, 50 mL) and theaqueous phase was extracted with CHCl3 (3 50 mL). The combinedextracts were dried with K2CO3 and evaporated to drynessto give 1,7-bis(tert-butoxycarbonyl)-1,4,7,10-tetraazacyclododecane(10) in quantitative yield.1,3,5-Tris(bromomethyl)benzene (7.65 g, 21.62 mmol) was dissolvedin CHCl3 (150 mL) and Na2CO3 (1.71 g, 16.15 mmol) wasadded. Compound 10 (1.08 g, 2.90 mmol) in CHCl3 (50 mL) wasadded dropwise into the reaction mixture during 11 hours at52 C. The reaction mixture was refluxed for 3 days at 62 C,filtrated, and evaporated to dryness. The residue was purified bysilica gel chromatography (40-70% EtOAc in hexane), giving 11 in27% yield (0.722 g). 1H NMR (500 MHz, CDCl3) d 7.33 (s, 6H), 4.45(s, 8H), 3.71 (s, 4H), 3.21-3.57 (m, 8H), 2.55-2.68 (m, 8H), 1.27(s, 18H). 13C NMR (100 MHz, CDCl3) dppm 155.8, 140.8, 138.5,129.9, 128.3, 79.3, 59.5, 55.2, 46.1, 32.9, 28.4. HRMS(ESI): obsd.921.0840 [M+H]+, Calcd. 921.0795 [M+H]+., 294-90-6

The synthetic route of 294-90-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Laine, Maarit; Loennberg, Tuomas; Helkearo, Mia; Loennberg, Harri; Inorganica Chimica Acta; vol. 452; (2016); p. 111 – 117;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI