HCID 58046435, compound → (1S,6R)-6-amino-2,2-difluorocyclohexanol
Reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C@@H](C2C=CC=CC=2)C)[C@@H:3]1[OH:17]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:4]1[C@H:3]([OH:17])[C:2]([F:18])([F:1])[CH2:7][CH2:6][CH2:5]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).