Hydrochloric Acid → 1-{[(Benzyloxy)amino]methyl}cyclopentane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(benzyloxyimino-methyl)-cyclopentanecarboxylic acid (1.91 g, 7.72 mmol) in methanol (70 mL) at 0° C. under a nitrogen atmosphere was added a trace amount of methyl orange. A solution of saturated methanolic HCl was added until a persistent red color was observed. Sodium cyanoborohydride (0.58 g, 9.27 mmol) was added portionwise alternately with methanolic HCl to maintain the red color. The reaction mixture was maintained at 0° C. for an additional 3 h and the volatiles were removed in vacuo. The residue was purified by preparative reverse-phase HPLC to yield the title compound as a pale, yellow oil (1.1 g, 57%). MH+250.

Provenance & Evidence