[1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl ester → 4-Amino-4-(4-fluorophenyl)cyclohexan-1-ol

HRID 2370298Notes

Reaction equation

HRID 2370298 reaction equation
C(OC(=O)[NH:10][C:11]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][C:11]1([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 59226075[1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl ester

Product 1

HCID 534025924-Amino-4-(4-fluorophenyl)cyclohexan-1-olYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.5 g of [1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl ester (78) were dissolved in 50 mL of methanol and 57 mg of palladium on charcoal (10%) were added. The mixture was stirred under a hydrogen atmosphere until conversion was complete. The catalyst was filtered off and the organic layer was evaporated to dryness to give 290 mg of the desired product. Rt=0.73 min (Method E). Detected mass: 175.2 (M+H—H2O—NH3+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe organic layer was evaporated to dryness

Sources & evidence

ORD record
ord-29f5c7d82f0242fd842ccb10bf8870f2
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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