Hydrochloric Acid → 2-Butyl-3-oxo-1,2,3,4,5,6,7,8-octahydroisoquinoline-4-carbonitrile
Reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]([C:16]#[N:17])=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:6]1)[CH2:2][CH2:3][CH3:4].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:14](=[O:15])[CH:13]([C:16]#[N:17])[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH2:6]1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Butyl-3-oxol-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-012) (100 mg, 0.43 mmol) was dissolved in toluene (10 mL), and to the reaction mixture was added 1 M diisobutylaluminum hydride toluene solution (0.8 mL, 0.8 mmol) under ice-cooling, and the reaction mixture was stirred for 10 min. To the reaction mixture was added 1 mol/L diluted hydrochloric acid (5 mL), and the reaction mixture was extracted with ethyl acetate (10 mL), washed with brine (5 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate) to give 2-butyl-3-oxo-1,2,3,4,5,6,7,8-octahydroisoquinoline-4-carbonitrile (7-018) (70 mg, 70%) as a white powder.
Workup
- temperaturecooling
- extractionthe reaction mixture was extracted with ethyl acetate (10 mL)
- washwashed with brine (5 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (toluene/ethyl acetate)
Sources & evidence
- ORD record
- ord-33e35e03eb754e608ac1b0458c5bd261
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088924B2
Reaction notes
Loading…