Methanol → Methyl (1S,3R)-3-aminocyclohexane-1-carboxylate

Participants

Reaction Steps

Thionyl chloride (0.6 ml) was added to solution of cis-3-amino-cyclohexanecarboxylic acid (bought from AMRI, USA, cat.-no.: A00342, 0.50 g, 2.80 mmol) in MeOH (20 ml) at 0° C. and stirred at reflux for 12 h. The volatiles were evaporated in vacuo and the resulting residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The separated organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuo to afford 400 mg (90.9%) of cis-methyl 3-aminocyclohexanecarboxylate as colorless liquid.

Provenance & Evidence