Cyclohexanone → HCID 68715687, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3-amino-phenyl)-tert-butoxycarbonylamino-acetic acid methyl ester (165 mg, CAS 180081-34-9) in MeOH (5 ml) was treated under an argon atmosphere with cyclohexanone (0.07 ml), zinc chloride (321 mg) and NaBH3CN (111 mg) and stirred overnight at 40° C. The MeOH was distilled off. The residue was taken up in EtOAc and H2O. The aqueous phase was back extracted with EtOAc. The combined organics were washed with water, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 14:1) to give (RS)-tert-butoxycarbonylamino-(3-cyclohexylamino-phenyl)-acetic acid methyl ester (200 mg, 94%) as viscous colorless oil.

Provenance & Evidence