3-(6-Methoxy-cyclohex-1-enyl)-1H-indole → 3-(2-Methoxy-cyclohexyl)-1H-indole

HRID 736966

Reaction equation

HRID 736966 reaction equation
[CH3:1][O:2][CH:3]1[C:8]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[CH:7][CH2:6][CH2:5][CH2:4]1>CCOC(C)=O.[Pd]>[CH3:1][O:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 1

HCID 589750733-(6-Methoxy-cyclohex-1-enyl)-1H-indole

Product 1

HCID 589750943-(2-Methoxy-cyclohexyl)-1H-indoleYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Treat 3-(6-methoxy-cyclohex-1-enyl)-1H-indole (200 mg, 0.879 mmol) with 10% Pd/C (40 mg) in EtOAc under atmospheric hydrogenation conditions for 1.5 hours. Filter resulting solution over Celite to remove catalyst. Concentrate crude on rotovap and purify on silica gel chromatography to give 3-(2-Methoxy-cyclohexyl)-1H-indole (127 mg, 63% yield). Mass Spectrum (m/e): 230.03 (MH+), 228.14 (M−).

Workup

  1. filtrationFilter
  2. customresulting solution over Celite
  3. customto remove catalyst
  4. concentrationConcentrate crude on rotovap
  5. custompurify on silica gel chromatography

Sources & evidence

ORD record
ord-683d20d846bf496d957543d5f33f089d
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Linked notes

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