3-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid → 3-cyclohexyl-1H-indole-6-carboxylic Acid

HRID 1713921Notes

Reaction equation

HRID 1713921 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

Product 1

HCID 112419893-cyclohexyl-1H-indole-6-carboxylic AcidYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution (0.5 M) of 3-cyclohexenyl-1H-indole-6-carboxylic acid (from Step 1) in THF/MeOH (0.5 M, 1:1, v/v) was hydrogenated for 14 h over Pd(OH)2/C (0.1 eq., 20%) at 60 psi. The catalyst was removed by filtration on a pad of Celite™ and the filtrate evaporated to dryness to afford 3-cyclohexyl-1H-indole-6-carboxylic acid (90%) as a white solid. 1H NMR (300 MHz, DMSO-d6, 300 K) δ 1.20-1.53 (m, 5H), 1.70-1.87 (m, 3H), 1.90-2.02 (m, 2H), 2.69-2.86 (m, 1H), 7.40 (s, 1H), 7.55-7.65 (m, 2H), 8.0 (s, 1H), 11.40 (s, 1H); MS (ES+) m/z 244 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration on a pad of Celite™
  2. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-f69ce567bd3e4d089d6f829e3f390a73
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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