HCID 178418361, compound → HCID 178461148, compound

HRID 2389196Notes

Reaction equation

HRID 2389196 reaction equation
[F:1][C:2]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11]CC2C=CC=CC=2)[CH2:7][CH2:6]1)([F:4])[CH3:3].[H][H]>CO.[Pd]>[F:1][C:2]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1)([F:4])[CH3:3]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178461149HCID 178461149, compound

Product 1

HCID 178461148HCID 178461148, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compounds ((cis-4-(1,1-difluoroethyl)cyclohexyloxy)methyl)benzene (480 mg, 1.89 mmol) and Pd—C (2.0 g, 0.38 mmol, 0.2 eq.) were dissolved in CH3OH (20 mL). Then the mixture was stirred at 50° C. under 40 atm. of hydrogen atmosphere for 6 h. When the reaction completed by TLC, the mixture was filtrated and the filtrate was concentrated and purified by silica gel column chromatography using petroleum ether/ethyl acetate (10/1) as eluent to give product (140 mg, 45%) as a slight yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.07-4.05 (m, 1H), 1.86-1.83 (m, 2H), 1.75-1.72 (m, 2H), 1.63-1.48 (m, 8H).

Workup

  1. filtrationthe mixture was filtrated
  2. concentrationthe filtrate was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6cb421090e1c4a11983bd6403520218c
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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