4-Methyl-2-{5-[1-(4-methyl-pent-2-enyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester → 4-Methyl-2-{5-[1-(4-methyl-pentyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester

HRID 889761Notes

Reaction equation

HRID 889761 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([C:10]1[CH:11]=[C:12]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][CH:25]([CH3:27])[CH3:26])[CH2:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]>CO>[CH2:1]([O:3][C:4](=[O:38])[CH:5]([C:10]1[CH:11]=[C:12]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:32][CH:33]=2)[CH:13]=[C:14]([CH:16]2[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:20][CH2:21]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

3

Reactant 1

HCID 666982724-Methyl-2-{5-[1-(4-methyl-pent-2-enyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester

Product 1

HCID 576659734-Methyl-2-{5-[1-(4-methyl-pentyl)-piperidin-4-yl]-4'-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of a mixture of 4-methyl-2-{5-[1-(4-methyl-pent-2-enyl)-piperidin-4-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester and methyl ester (69a) (25 mg, 0.05 mmol) in MeOH (2.0 mL) was flushed with N2. To this was added 10% Pd/C (5 mg). The suspension was hydrogenated at 20 psi for 4 h at room temperature. It was filtered through celite and the solid was washed with EtOAc. The filtrate was dried (MgSO4) and concentrated in vacuo to obtain 4-methyl-2-{5-[1-(4-methyl-pentyl)-piperidin-4-yl]-4′-trifluoromethyl-biphenyl-3-yl}-pentanoic acid ethyl ester and methyl ester. Calcd for C31H42F3NO2 (M+H) 518.67, Found 518.3 (methyl ester) and Calcd for C32H44F3NO2 (M+H) 532.69, Found 532.4 (ethyl ester).

Workup

  1. customwas flushed with N2
  2. additionTo this was added 10% Pd/C (5 mg)
  3. filtrationIt was filtered through celite
  4. washthe solid was washed with EtOAc
  5. dry with materialThe filtrate was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0f8bd58c8364a7daac3a813c5fff830
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

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