Tetrahydrofuran → HCID 59216387, compound

HRID 2069810Notes

Reaction equation

HRID 2069810 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4([C:21]#N)[CH2:20][CH2:19]4)[CH:14]=3)[C:9]2=[O:23])=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.C1C[O:38]CC1>ClCCl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4([CH:21]=[O:38])[CH2:20][CH2:19]4)[CH:14]=3)[C:9]2=[O:23])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 59216374HCID 59216374, compound

Product 1

HCID 59216387HCID 59216387, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 722 mg of 1-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-cyclopropanecarbonitrile in 3 ml of dichloromethane and 9 ml toluene, cooled at −50° C. was added dropwise 4.8 mL of 1.0 M DIBAL in THF. After stirring 1 hour at −50° C., the reaction was quenched with 5 ml of 1N HCl, left to warm to room temperature and stirred 0.5 hour. Next the mixture was extracted with ethyl acetate and the organic layer was washed with 0.5 N HCl, sodium carbonate 5% solution, and brine. After drying over sodium sulfate and removal of solvent in vacuo, the residue was purified by silica gel column chromatography using 30%-60% ethylacetate in hexane to provide 0.075 g of 1-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-cyclopropanecarbaldehyde.

Workup

  1. customthe reaction was quenched with 5 ml of 1N HCl
  2. waitleft
  3. temperatureto warm to room temperature
  4. stirringstirred 0.5 hour
  5. extractionNext the mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with 0.5 N HCl, sodium carbonate 5% solution, and brine
  7. dry with materialAfter drying over sodium sulfate and removal of solvent in vacuo
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-964a190b9c694f27b4077d1d77a77944
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…