Acetic Acid → tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

Participants

Reaction Steps

2.7 g (0.0714 mol) of sodium borohydride are added in portions to a solution of 3.8 g (0.018 mol)of N-BOC-2-azabicyclo[2.2.1 ]heptan3-one in 125 ml of methanol in the course of 20 minutes, while stirring and cooling in an ice-bath. The reaction mixture is further stirred at 0° C. for 1 hour and at room temperature for 1 hour, a solution of 4.08 ml (0.0714 mol) of acetic acid in 8 ml of methanol is then added dropwise and the mixture is evaporated to dryness in vacuo. The crystalline residue is partitioned between methylene chloride and water. After the organic phase has been washed with brine, dried over sodium sulfate and evaporated in vacuo, the title compound is obtained as crystalline residue, m.p. 73°-74° C.

Provenance & Evidence