Triethylamine → 2-(3-Phenyl-propyl)-6-(3,3-diacetoxy-1-propen-1-yl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 1741703Notes

Reaction equation

HRID 1741703 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=3)[C:11]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([O:25][CH:26]([O:29][C:30](=[O:32])[CH3:31])[CH:27]=[CH2:28])(=[O:24])[CH3:23].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].CC#N>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:28]=[CH:27][CH:26]([O:25][C:22](=[O:24])[CH3:23])[O:29][C:30](=[O:32])[CH3:31])[CH:16]=3)[C:11]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 612263,3-DiacetoxypropeneHCID 80271Tri-o-tolylphosphineHCID 189639072-(3-Phenylpropyl)-6-bromo-1-oxo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 543550622-(3-Phenyl-propyl)-6-(3,3-diacetoxy-1-propen-1-yl)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a sealed tube apparatus is added 2-(3-phenylpropyl)-6-bromo-1-oxo-1,2,3,4-tetrahydroisoquinoline (1.6 g, 4.65 mmol), CH3CN (8 mL), 1,1-diacetoxy-2-propene (3.4 mL, 23.25 mmol), Pd(OAc)2 (84 mg, 0.37 mmol), P(o-tolyl)3 (113 mg, 0.37 mmol) and Et3N 0.78 mL, 5.58 mmol). The reaction vessel is then sealed and the mixture heated to 120° for 48 hours. After cooling to ambient temperature the reaction mixture is diluted with EtOAc (150 mL) and filtered through Celite. The organic phase is washed with saturated NaCl solution (2×200 mL), dried over MgSO4 and concentrated in vacuo. The residue is chromatographed (silica gel, 9:1 hexane/EtOAc, 1:1 hexane/EtOAc, 1:1 hexane/EtOAc) to give 2-(3-phenylpropyl)-6-(3,3-diacetoxy-1-propen-1-yl)-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customThe reaction vessel is then sealed
  2. temperaturethe mixture heated to 120° for 48 hours
  3. filtrationfiltered through Celite
  4. washThe organic phase is washed with saturated NaCl solution (2×200 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed (silica gel, 9:1 hexane/EtOAc, 1:1 hexane/EtOAc, 1:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-2b717e9e7a0345149f4ffea0155249e8
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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