tert-butyl (3R)-3-({[(benzyloxy)carbonyl]amino}methyl)pyrrolidine-1-carboxylate synthesis

Yield:879275-54-4 77%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 0; for 4 h;

Steps:

306

A solution of (R)-tert-butyl 3-(aminomethyl)pyrrolidine-l-carboxylate (1.0 g, 5.0mmol) and 50 mL THF was cooled in an ice bath. To this mixture was added benzylchloro'forma'te' (W?M?5S mmol)/lWlbwed by triethylamine (1.39 mL, 10 mmol). After removing the ice bath, the reaction was stirred for 4 h. The mixture was poured into ice water and extracted with EtOAc. The organic extracts were washed with water, dried over Na2SC>4, filtered, and concentrated. Purification via silica gel chromatography using EtOAc in hexanes (0^40%) gave benzyl ((i?)-l-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylcarbamate (1.29 g, 77%) as a colorless oil. ^.H NMR (400 MHz, CDC1₃) 5 7.39-7.28 (m, 5H), 5.10 (s, 2H), 4.87 (s, 1H), 3.52-2.95 (m, 6H), 2.41-2.35 (m, 1H), 2.10-1.79 (m, 2H), 1.45 (s, 9H).

References:

WO2006/28904,2006,A1 Location in patent:Page/Page column 331-332