HCID 66783041, compound → HCID 57475067, compound

HRID 1095574Notes

Reaction equation

HRID 1095574 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][C:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH2:4]1.[H][H]>[Pd].CO>[CH3:30][N:2]([CH3:1])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 66783041HCID 66783041, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57475067HCID 57475067, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Palladium as the catalyst (Pd/C, 5%, 200 mg) was added to (±)-4-[2-(-4-dimethylamino-4-phenyl-cyclohex-1-enyl)-1H-indol-3-yl]butanoic acid (500 mg, 1.2 mmol) in abs. methanol (50 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-Dimethylamino-4-phenylcyclohexyl)-1H-indol-3-yl]butanoic acid was obtained in a yield of 340 mg (68%) as a white 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-1226be422d4b4eb6b5539c61d4c6cd36
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…