HCID 68577761, compound → HCID 68578639, compound

HRID 886946Notes

Reaction equation

HRID 886946 reaction equation
[CH3:1][C:2]([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)=[CH2:3]>[Pd].CO>[CH3:3][CH:2]([C:4]1[C:14]2[O:13][CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:1]

Participants

4

Reactant 1

HCID 68577761HCID 68577761, compound

Product 1

HCID 68578639HCID 68578639, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 9-(1-methylethenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (480 mg, 1.66 mmol) and 10% palladium on carbon (30.0 mg) in methanol (10 ml) was stirred under a hydrogen atmosphere for 12 hr. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired product (330 mg, 68.1%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-3e4ec9a174e948cc9fb48eb386981a55
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

Loading…