Bromoform → 3-(Tert-butoxycarbonylamino)-1-(3-fluorophenoxy)cyclohexanecarboxylic acid

Participants

Reaction Steps

To the mixture of tert-butyl 3-oxocyclohexylcarbamate (5 mmol, 1.065 g), 3-fluorophenol (5 mmol, 560 mg) and NaOH (25 mmol, 1 g) in THF at 0° C. was added bromoform (25 mmol, 2.2 mL) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for overnight. The reaction mixture was concentrated. The product, 3-(tert-butoxycarbonylamino)-1-(3-fluorophenoxy)cyclohexanecarboxylic acid, was obtained (60 mg, 3% yield) after purification by reverse phase HPLC.

Provenance & Evidence