Benzyl (3,3-difluorocyclohexyl)carbamate → HCID 86702151, compound

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Reaction Steps

To a suspension of benzyl (3,3-difluorocyclohexyl)carbamate (0.43 g, 1.6 mmol) in 4% formic acid in methanol (25 mL) was added 10% palladium on carbon (0.4 g, 50% wet). The resulting mixture stirred under an atmosphere of hydrogen for 20 hrs. The mixture was filtered through Celite, washing with methanol, and concentrated under vacuum to give an off-white solid (0.3 g). 1H NMR (d6-DMSO, 300 MHz) δ 8.36 (s, 1H), 3.03 (m, 1H), 2.97 (m, 1H), 1.97-1.63 (m, 5H), 1.39-1.22 (m, 2H). 19F NMR (d6-DMSO, 400 MHz) −60.33-−60.97 (d, 1F, J=252 Hz), −70.73-71.54 (dt, 1F, J=252, 36 Hz). ESI (m/z) 136.2 (M+H).

Provenance & Evidence