HCID 66815868, compound → HCID 59859863, compound

HRID 1944531Notes

Reaction equation

HRID 1944531 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:10][CH2:9]2>CO.[Pd]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[CH2:10][CH2:9]2

Participants

4

Reactant 1

HCID 66815868HCID 66815868, compound

Product 1

HCID 59859863HCID 59859863, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(1-cyclohexyl-2,3-dihydro-1H-indol-5-yl)-acrylic acid methyl ester (1.60 g, 5.61 mmol) in methanol (30 mL) with 10% palladium on carbon (0.16 g) was hydrogenated at 55 psi and room temperature for 20 hours. The catalyst was removed by filtration, and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography, using 7.5% ethyl acetate in hexane as the eluant, to give the product, 1.36 g (84%), an oil. MS: m/z 288 (MH+). 1H NMR (CDCl3): 1.04-1.21 (m, 1 H), 1.26-1.43 (m, 4 H), 1.64-1.73 (m, 1 H), 1.78-1.86 (m, 4 H), 2.82 (t, 2 H), 2.84-2.92 (m, 4 H), 3.29 (m, 1 H) super imposed on 3.34 (t, 2 H), 3.66 (s, 3 H), 6.31 (d, 1 H), 6.85 (d, 1 H) and 6.87 (s, 1 H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated in vacuo
  3. customThe crude product was purified by flash chromatography
  4. customto give the product, 1.36 g (84%)

Sources & evidence

ORD record
ord-992c17d234784e6ca1b26ca126493784
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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