(S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate → (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate

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Reaction Steps

A mixture of (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate (13.6 g, 0.048 mol) and Pd/C (1.4 g) in methanol (200 mL) was hydrogenated with a balloon overnight. The mixture was filtered through a pad of Celite and the solvent was removed to give (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate (10.5 g, 86%), which was used in the next step without purification. 1H NMR (400 MHz, CDCl3): 4.52 (d, J=8.4 Hz, 1H), 3.68 (m, 2H), 2.73 (dd, J=13.6&4.4 Hz, 1H), 2.58 (dd, J=13.6&6.0 Hz, 1H), 1.81 (m, 1H), 1.65 (m, 4H), 1.42 (s, 9H), 1.40-1.00 (m, 6H), 1.00-0.70 (m, 2H). MS (E/Z): 257 (M+H+).

Provenance & Evidence