HCID 68579379, compound → HCID 68578722, compound

HRID 886937Notes

Reaction equation

HRID 886937 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[C:16]2[O:15][CH2:14][CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][C:10]=2[CH:9]=[CH:8][CH:7]=1>[Pd].CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:16]2[O:15][CH2:14][CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 68579379HCID 68579379, compound

Product 1

HCID 68578722HCID 68578722, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 9-[(1E)-3-methoxypropa-1-ene-1-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (200 mg, 0.622 mmol) and 10% palladium on carbon (50.0 mg) in methanol (4 ml) was stirred under a hydrogen atmosphere for 12 hr. The reaction mixture was filtered, and the filtrate was concentrated. The residue was poured into water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the desired product (170 mg, 85.0%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was poured into water
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf836b22b7304608a30fb50ac19ca5d0
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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