HCID 10345144, compound → 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone

HRID 2357474Notes

Reaction equation

HRID 2357474 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1>[Pd].CO>[CH3:33][N:2]([CH3:1])[C:3]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:19][CH:18]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 10345144HCID 10345144, compound

Product 1

HCID 103452162-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanoneYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (5%, 60 mg) was added to a solution of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone (605 mg, 1.36 mmole) in abs. methanol (100 ml). The reaction mixture was hydrogenated for 23 hours at RT under a pressure of 3 bar. The catalyst was separated using Celite and the filtrate was concentrated by evaporation. After chromatographic separation of the residue (579 mg) on silica gel (50 g) with EE/methanol (2:1) the non-polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone was isolated in a yield of 31% (190 mg), and the polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone was isolated in a yield of 64% (386 mg). Both compounds were colourless oils.

Workup

  1. customThe catalyst was separated
  2. concentrationthe filtrate was concentrated by evaporation
  3. customAfter chromatographic separation of the residue (579 mg) on silica gel (50 g) with EE/methanol (2:1) the non-polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-1-[3-(1H-indol-3-yl)pyrrolidine-1-yl]-ethanone
  4. customwas isolated in a yield of 31% (190 mg)

Sources & evidence

ORD record
ord-1f57ed9a4f7045bb8c6c1da454c11776
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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