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

HRID 1776228Notes

Reaction equation

HRID 1776228 reaction equation
[F:1][C:2]1([F:19])[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:18])[O:10]CC2C=CC=CC=2)[CH2:3]1>C(O)=O.CO.[Pd]>[CH:9]([O-:18])=[O:10].[F:1][C:2]1([F:19])[CH2:7][CH2:6][CH2:5][CH:4]([NH3+:8])[CH2:3]1

Participants

5

Reactant 1

HCID 70316560Benzyl (3,3-difluorocyclohexyl)carbamate

Product 1

HCID 86702151HCID 86702151, compoundYield 103.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

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).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashing with methanol
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-121778d1718a4186a3d44d8b27b33f42
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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