Lithium borohydride → HCID 13008958, compound

Participants

Reaction Steps

Add lithium borohydride (0.16 mol, 3.6 g) to a solution of (2S,4S)-4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.16 mol, 40 g) in anhydrous diethyl ether (400 mL) at −10 to −20° C. under a nitrogen atmosphere. Upon complete addition, stir the reaction mixture for 30 min at the same temperature. Quench the reaction mixture with saturated sodium bicarbonate solution at −70° C. and allow it to come to room temperature slowly. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under vacuum to obtain the title compound (32 g, crude) as a thick, yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 2.32-2.35 (m, 1H), 3.30 (dd, 1H), 3.65-3.79 (m, 4H), 4.07-4.29 (m, 2H).

Provenance & Evidence