Lithium Hydroxide → tert-butyl ((1S,2R)-2-hydroxycyclohexyl)carbaMate

Participants

Reaction Steps

To a stirred solution of (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate (1.95 g, 5.35 mmol) in THF (50 mL) was added a solution of 1N LiOH (9.63 mL, 9.63 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours and then partitioned between EtOAc and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 1:1) to give tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 100%).

Provenance & Evidence