tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate → tert-Butyl ((1R,2R)-2-amino-3,3-difluorocyclohexyl)carbamate

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Reaction Steps

A solution of tert-butyl [(1R,6R)-2-azido-3,3-difluorocyclohexyl]carbamate 28 (0.94 g, 3.40 mmol) in methanol (20 mL) was degassed with nitrogen and treated with 10% Pd/C (72 mg). The resulting heterogenous solution was exposed to a hydrogen atmosphere and stirred vigorously for 16 hours. The reaction was filtered, washing with methanol, and evaporated in vacuo to give 0.78 g (91%) of tert-butyl [(1R,2R)-2-amino-3,3-difluorocyclohexyl]carbamate 29 as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 6.67 (1H, d, J=8.3 Hz), 3.55 (1H, bs), 3.07 (1H, bs), 2.03 (1H, m), 1.62 (3H, m), 1.45 (1H, m), 1.36 (12H, m).

Provenance & Evidence