Ammonium Hydroxide → HCID 59593777, compound

Participants

Reaction Steps

A solution of tert-butyl((1R)-1-methyl-1-oxiran-2-yl-2-phenylethyl)carbamate (986 mg, 3.56 mmol) in EtOH (35 mL) and NH4OH (35 mL) was stirred at 60° C., sealed, for 16 h, concentrated in vacuo and purified by flash chromatography (silica, 0-30% (10% NH4OH/MeOH)/CH2Cl2) to provide tert-butyl ((1R)-3-amino-1-benzyl-2-hydroxy-1-methylpropyl)carbamate as a thick oil. 1H NMR (400 MHz, CD3OD, 1:1 diastereomeric mixture) δ 7.30-7.14 (m, 5H), 4.01 (br d, J=9.2 Hz, 0.5H), 3.54 (dd, J=10.0, 2 Hz, 0.5H), 3.39 (br s, 0.5H), 3.36 (br s, 0.5H), 2.94-2.56 (m, 4H), 1.47 (s, 9H), 1.03 (s, 1.5H), 0.99 (s, 1.5H).

Provenance & Evidence