Tetrahydrofuran → cis-4-(Boc-amino)-1-methylcyclohexanol

Participants

Reaction Steps

To a 6 ml anhydrous tetrahydrofuran solution of 303 mg (1.42 mmol) of tert-butyl N-(4-oxocyclohexyl)carbamate, 2.7 ml of methyl lithium (1.1M in hexane, 2.98 mmol) was dropwise added at −78° C. under an argon atmosphere and stirred for 1.5 hours, after adding 20 ml of water thereto to return room temperature, followed by extracting with 30 ml of methylene chloride after drying over anhydrous sodium sulfate, the solvent was distilled off and the residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain 150 mg (46%) of non-polar side diastereomer as a colorless crystal and 54 mg (17%) of polar side diastereomer as a colorless crystal.

Provenance & Evidence