HCID 68191980, compound → Ethyl 3-(1-(4-fluorophenyl)cyclohexyl)propanoate

HRID 1506287Notes

Reaction equation

HRID 1506287 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68191980HCID 68191980, compound

Product 1

HCID 67168455Ethyl 3-(1-(4-fluorophenyl)cyclohexyl)propanoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-ethyl 3-(1-(4-fluorophenyl)cyclohexyl)acrylate (Intermediate I-7B, 1 g, 3.62 mmol) in methanol (25 mL) was added 10% Pd/C (˜0.5 g, wet 50%) under argon, and the mixture was stirred under hydrogen atmosphere (50 psi) for 16 hrs. The reaction mixture was filtered through CELITE® and evaporated to give the desired ethyl 3-(1-(4-fluorophenyl)cyclohexyl)propanoate (1 g, 99% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.25 (2H, dd, J=9.02, 5.28 Hz), 7.00 (2H, t, J=8.80 Hz), 4.02 (2H, q, J=7.26 Hz), 2.00-2.08 (2H, m), 1.89-1.96 (2H, m), 1.81-1.87 (2H, m), 1.34-1.61 (8H, m), 1.18 (3H, t, J=7.15 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. customevaporated

Sources & evidence

ORD record
ord-b6ab9930af694c16bd91ebad2fee7015
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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