HCID 68579338, compound → HCID 68579772, compound

HRID 886934Notes

Reaction equation

HRID 886934 reaction equation
[CH:1]([C:3]1[C:13]2[O:12][CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH2:2]>[Pd].CO>[CH2:1]([C:3]1[C:13]2[O:12][CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 68579338HCID 68579338, compound

Product 1

HCID 68579772HCID 68579772, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 9-ethenyl-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (349 mg, 1.27 mmol) and 10% palladium on carbon (50.0 mg) in methanol (6 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 (260 mg, 73.9%) 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-5025ab6310784a6ba0b1c580821b9062
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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