HCID 18378604, compound → HCID 18378582, compound

HRID 2298808Notes

Reaction equation

HRID 2298808 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:18]=[C:17]([C:19]([N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25](=O)[CH2:24][CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:18]=[C:17]([C:19]([N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25](=[CH2:1])[CH2:24][CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 2

HCID 18378604HCID 18378604, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18378582HCID 18378582, compoundYield 21.8%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyltriphenylphosphonium bromide (607 mg) in N,N-dimethylformamide (10 ml) was added potassium-tert-butoxide (191 mg), and the mixture was stirred at room temperature for 30 minutes. Methyl 2-methoxy-4-(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonylbenzoate (300 mg) was added to the resulting solution, and the mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and the solution was washed successively with 1N hydrochloric acid, water and brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated in vacuo to give an oil. The crude product was purified by silica gel column chromatography (10% ethyl acetate in hexane) to give methyl 2-methoxy-4-(2,3,4,5-tetrahydro-5-methylene-1H-1-benzazepin-1-yl)carbonylbenzoate (65 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe solution was washed successively with 1N hydrochloric acid, water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customto give an oil
  6. customThe crude product was purified by silica gel column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5b8a3695cbad4e34b66b2498c4c82f7e
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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