Sodium cyanoborohydride → tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamate

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Reaction Steps

To a stirred solution of (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (193 mg, 0.43 mmol) and NH4OAc (670 mg, 8.6 mmol) in MeOH (15 mL) was added NaCNBH3 (270 mg, 4.3 mmol). The mixture was heated at reflux for 22 h and concentrated under reduced pressure. The residue was partitioned between 1 M aq NaOH (25 mL) and CH2Cl2 (2×50 mL). The combined CH2Cl2 layers were washed with brine (15 mL), dried over Na2SO4 and concentrated to afford tert-butyl 4-amino-4-phenylbutyl((1S)-1-(4-bromophenyl)ethyl)carbamate (179 mg, 93%) as an oil which was used without further purification. LC-MS Method 1 tR=1.57 min, m/z=449, 447.

Provenance & Evidence