Water → HCID 53737182, compound

HRID 1590189Notes

Reaction equation

HRID 1590189 reaction equation
[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]([CH2:12][CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:11].C(N(CC)CC)C.[CH2:32](Br)[CH2:33][CH3:34].O>CN(C)C=O>[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]([CH2:12][CH:13]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)[C:14]([O:16][CH2:32][CH2:33][CH3:34])=[O:15])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 8471TriethylamineHCID 53849277HCID 53849277, compound

Product 1

HCID 53737182HCID 53737182, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(4-methylbenzyl)propionic acid (100 mg) in N,N-dimethylformamide (2 ml) were added triethylamine (50 mg) and propyl bromide (100 mg) and the mixture was stirred at room temperature for 15 hours. To the reaction mixture was added water (10 ml) and the mixture was extracted with ethyl acetate. The organic layer was washed succesively with 1N hydrochloric acid, saturated sodium bicarbonate solution, and brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (4/1) to give 30 mg of propyl 3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(4-methylbenzyl)propionate as a colorless viscous oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed succesively with 1N hydrochloric acid, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried over MgSO4
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record
ord-060562d500a94062842dddef11dfdd2d
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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