(1S,6R)-6-amino-2,2-difluorocyclohexan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S,6R)-2,2-difluoro-6-{[(1R)-1-phenylethyl]amino}cyclohexanol (2.0 g, 7.8 mmol) in methanol (100 mL) was degassed with nitrogen, treated with Pd(OH)2/C (0.55 g) and then placed under an atmosphere of hydrogen and stirred vigorously for 16 hours. The reaction was filtered, washed with methanol, and the filtrate evaporated in vacuo to afford the title compound as a white solid: 1H NMR (500 MHz, CD3OD) δ 3.34 (m, 1H); 2.74 (m, 1H); 2.07 (m, 1H); 1.89 (m, 1H); 1.73 (m, 2H); 1.50 (m, 1H); 1.27 (m, 1H). The reaction was filtered washed with methanol the filtrate evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S,6R)-2,2-difluoro-6-{[(1R)-1-phenylethyl]amino}cyclohexanol 23 (2 g, 7.83 mmol) in methanol (100 mL) was degassed with nitrogen, treated with Pd(OH)2/C (0.55 g) and then placed under an atmosphere of hydrogen and stirred vigorously for 16 hours. The reaction was filtered, washing with methanol, and evaporated in vacuo to give 1.0 g (84%) of (1S,6R)-6-amino-2,2-difluorocyclohexanol 24 as a white solid: 1H NMR (500 MHz, CD3OD) δ 3.34 (1H, m), 2.74 (1H, m), 2.07 (1H, m), 1.89 (1H, m), 1.73 (2H, m), 1.50 (1H, m), 1.27 (1H, m). The reaction was filtered washing with methanol evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S,6R)-2,2-difluoro-6-{[(1R)-1-phenylethyl]amino}cyclohexanol 31 (2 g, 7.83 mmol) in methanol (100 mL) was degassed with nitrogen, treated with Pd(OH)2/C (0.55 g) and then placed under an atmosphere of hydrogen and stirred vigorously for 16 hours. The reaction was filtered, washing with methanol, and evaporated in vacuo to give 1.0 g (84%) of (1S,6R)-6-amino-2,2-difluorocyclohexanol 32 as a white solid: 1H NMR (500 MHz, CD3OD) δ 3.34 (1H, m), 2.74 (1H, m), 2.07 (1H, m), 1.89 (1H, m), 1.73 (2H, m), 1.50 (1H, m), 1.27 (1H, m). The reaction was filtered washing with methanol evaporated in vacuo