Formic Acid → 1,1-Dimethylethyl N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamate

Participants

Reaction Steps

(3S)-3-tert-Butoxycarbonylamino-1-chloro-4-phenyl-2-butanone (1.49 g, 5.0 mmol), 90% formic acid (0.224 ml, 5.25 mmol), and triethylamine (0.730 ml, 5.25 mmol) were added to a solution of chloro(pentamethylcyclopentadienyl)rhodium (III) (1R,2R)-N-(p-toluenesulfonyl-1,2-diphenylethylenediamine (3.4 mg, 0.005 mmol, s/c=1000) in ethyl acetate (7.0 ml), followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction mixture was quantitatively analyzed by HPLC to confirm production of a desired compound, (2R, 3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4phenylbutane (1.50 g; yield: 99.9%). The production ratio of the desired (2R,3S)-form to the isomeric (2S,3S)-form, (2R,3S):(2S,3S), was found to be 9.0:1.

Provenance & Evidence