HCID 57475167, compound → HCID 57475065, compound

HRID 1095572Notes

Reaction equation

HRID 1095572 reaction equation
[CH2:1]([C:8]1([N:29]([CH3:31])[CH3:30])[CH2:13][CH2:12][C:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[CH2:1]([C:8]1([N:29]([CH3:31])[CH3:30])[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 57475167HCID 57475167, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57475065HCID 57475065, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Palladium as the catalyst (Pd/C, 5%, 120 mg) was added to 4-[2-(4-benzyl-4-dimethylaminocyclohex-1-enyl)-1H-indol-3-yl]butanoic acid (300 mg, 0.7 mmol) in abs. methanol (30 ml) and hydrogenation was carried out at RT for 6 h (hydrogen pressure: 3 bar). The catalyst was removed with the aid of a frit provided with a layer of Celite 1 cm high. The residue was rinsed thoroughly with methanol (500 ml). The solvent was distilled off in vacuo. 4-(2-(4-Benzyl-4-(dimethylamino)cyclohexyl)-1H-indol-3-yl)butanoic acid was obtained in a yield of 260 mg (86%) as a yellow solid (one of the two possible diastereoisomers).

Workup

  1. customThe catalyst was removed with the aid of a frit
  2. customprovided with a layer of Celite 1 cm high
  3. washThe residue was rinsed thoroughly with methanol (500 ml)
  4. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-d876b659ddcf4653af9fc3f4f02b3821
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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