Water → HCID 86746701, compound

HRID 1590177Notes

Reaction equation

HRID 1590177 reaction equation
C[C:2]1[CH:24]=C[C:5](/[CH:6]=[C:7](\[CH2:11][C:12]([N:14]2[CH2:22][C@H:21]3[C@H:16]([CH2:17][CH:18]=[CH:19][CH2:20]3)[CH2:15]2)=O)/C(O)=O)=[CH:4][CH:3]=1.[CH2:25](N(CC)CC)C.[CH2:32](Br)[CH2:33][CH3:34].[OH2:36].CN(C)[CH:39]=[O:40]>>[CH3:25][C:3]1[CH:2]=[CH:24][C:6](/[CH:7]=[C:11](\[CH2:12][N:14]2[CH2:15][C@H:16]3[C@H:21]([CH2:20][CH:19]=[CH:18][CH2:17]3)[CH2:22]2)/[C:39]([O:40][CH2:32][CH2:33][CH3:34])=[O:36])=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 78401-BromopropaneHCID 8471TriethylamineHCID 69054418HCID 69054418, compound

Product 1

HCID 86746701HCID 86746701, compound

Procedure

To a solution of (E)-2-(4-methylbenzylidene)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)-propionic acid (310 mg) in N,N-dimethylformamide (20 ml) were added triethylamine (105 mg) and propyl bromide (125 mg) and the mixture was stirred at room temperature for 15 hours. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively 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 165 mg of propyl (E)-2-(4-methylbenzylidene)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinyl)propionate as a colorless viscous oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively 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-41a2da60469f454aa6660c0ab8396870
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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