6-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester → 6-(4-Hydroxy-cyclohexyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester

HRID 1689778Notes

Reaction equation

HRID 1689778 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH:15]=3)=[CH:11][CH:12]=2)[N:7]([CH3:21])[CH:6]=1)=[O:4]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]3)=[CH:11][CH:12]=2)[N:7]([CH3:21])[CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 669063356-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester

Product 1

HCID 669060106-(4-Hydroxy-cyclohexyl)-1-methyl-1H-indole-3-carboxylic acid methyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester (0.251 g, 0.880 mmol) in tetrahydrofuran (10 mL) is added to a slurry of palladium (0.200 g, 5% in carbon) in THF (2 mL). The mixture is stirred under an atmosphere of hydrogen (balloon) at room temperature for 12 h. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to yield the title compound (0.202 g, 80%). MS m/z 288.3 (M+1)

Workup

  1. filtrationThe mixture is filtered through a pad of diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d429c7fb0e48497eb61b0fea5f9bed7c
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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