Phenol → HCID 86596952, compound

Participants

Reaction Steps

A solution of tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate (120 mg) in tetrahydrofuran (3 mL) was treated with phenol (45 mg) and triphenylphosphine (125 mg). The mixture was stirred at rt and treated dropwise over about 3 minutes with diethyl azodicarboxylate (74 μL). The mixture was stirred for 3.5 h, then was concentrated under vacuum. The residue was purified by flash chromatography on silica gel, eluting with 1:5 v/v ethyl acetate/hexane, to provide tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(phenoxymethyl)cyclohexylcarbamate as a white glassy foam (110 mg). MS found: (M+H)+=455.3.

Provenance & Evidence