Tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxy-pyrrolidine-1-carboxylate → 1-Methyl-4-(methylamino)pyrrolidin-3-OL

Participants

Reaction Conditions

Reaction Steps

LAH (1.40 g, 35.0 mmol) is slowly added to a stirred solution of 3-benzyloxycarbonylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester in THF (15 ml) at room temperature. The reaction mixture is heated to reflux under N2 for 2 hours and then cooled to 0° C. The reaction mixture is quenched by the slow addition of Na2SO4.10H2O, warmed to room temperature, diluted with ethyl acetate and filtered through Celite. The filtrate is concentrated and purified on a silica gel column (10:1:0.5 methylene chloride, MeOH, 30% NH4OH solution) to yield 0.21 g (18% for two steps) 1-methyl-4-methylamino-pyrrolidin-3-ol.

Provenance & Evidence