tert-butyl 9-(2-methylpropa-1-ene-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate → tert-butyl 9-(2-methylpropyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 886940Notes

Reaction equation

HRID 886940 reaction equation
[CH3:1][C:2]([CH3:22])=[CH:3][C:4]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1>[Pd].CO>[CH3:1][CH:2]([CH3:22])[CH2:3][C:4]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 68580669tert-butyl 9-(2-methylpropa-1-ene-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 68579404tert-butyl 9-(2-methylpropyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 9-(2-methylpropa-1-ene-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (270 mg, 0.890 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, 95.6%) 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-cdb1fb7738804feeba1cc71fb2065fd8
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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