HCID 68579627, compound → HCID 68577991, compound

HRID 886929Notes

Reaction equation

HRID 886929 reaction equation
[CH:1](/[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)=[CH:2]\[CH3:3]>[Pd].CO>[CH2:1]([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)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 68579627HCID 68579627, compound

Product 1

HCID 68577991HCID 68577991, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 9-[(1E)-propa-1-ene-1-yl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (170 mg, 0.587 mmol) and 10% palladium on carbon (100 mg) in methanol (5 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=2:1) to give the desired product (140 mg, 81.9%) 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=2:1)

Sources & evidence

ORD record
ord-7dbb2766ebfb4972935e1649f401019f
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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