HCID 59458431, compound → HCID 86702152, compound

HRID 1776230Notes

Reaction equation

HRID 1776230 reaction equation
[F:1][C:2]1([F:19])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][C:9](=[O:18])[O:10]CC1C=CC=CC=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][CH2:4][CH:3]1[NH3+:8]

Participants

5

Reactant 1

HCID 59458431HCID 59458431, compound

Product 1

HCID 86702152HCID 86702152, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of benzyl (2,2-difluorocyclohexyl)carbamate (0.200 g, 0.7 mmol) in 4% formic acid in methanol (10 mL) was added 10% palladium on carbon (0.15 g, 50% wet). The reaction mixture was stirred under an atmosphere of hydrogen for 18 hrs, filtered through Celite, washing with methanol, and concentrated under vacuum to give an off-white solid (0.1 g). 1H NMR (d6-DMSO, 300 MHz) δ 8.21 (s, 1H), 3.03-2.95 (m, 1H), 2.07-2.04 (m, 1H), 1.76-1.34 (m, 7H). ESI (m/z): 136.2 (M+H).

Workup

  1. filtrationfiltered through Celite
  2. washwashing with methanol
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fd2962184cee4dadbc6a7ecd1291b67a
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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