Cesium carbonate → 4-methoxybutyl 1-(4-methoxybutyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 1184057Notes

Reaction equation

HRID 1184057 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].CS(O[CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH3:23])(=O)=O.[C:24](=[O:27])([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.O>[CH3:23][O:22][CH2:21][CH2:20][CH2:19][CH2:18][N:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:10][CH2:2][CH2:3][CH2:4][O:27][CH3:24])=[O:11]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 7738064,5,6,7-Tetrahydro-1H-indole-2-carboxylic acidHCID 116870064-Methoxybutyl methanesulfonate

Product 1

HCID 583556924-methoxybutyl 1-(4-methoxybutyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylateYield 131.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid (280 mg), 4-methoxybutyl methanesulfonate (775 mg) and cesium carbonate (2.77 g) in N,N-dimethylacetamide (25 ml) was stirred at 65° C. for 15 hr. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-3:7) was concentrated under reduced pressure to give the object product (375 mg).

Workup

  1. extractionextracted with ethyl acetate (20 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (5:95-3:7)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-c47bd9925026429b93d169daa8230e07
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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