tert-butyl 8-ethenyl-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate → HCID 67959446, compound

HRID 1404979Notes

Reaction equation

HRID 1404979 reaction equation
[CH:1]([C:3]1[C:12]2[O:11][CH:10]([CH3:13])[CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7][C:6]=2[S:5][CH:4]=1)=[CH2:2]>C1COCC1.CO.[Pd]>[CH2:1]([C:3]1[C:12]2[O:11][CH:10]([CH3:13])[CH2:9][N:8]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:7][C:6]=2[S:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67958935tert-butyl 8-ethenyl-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 67959446HCID 67959446, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 8-ethenyl-2-methyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (231 mg) in THF-MeOH (2:1, 15 mL) was added 10% palladium on carbon (50 mg), and the mixture was stirred for 1 hr under a hydrogen atmosphere. The reaction solution was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→15% ethyl acetate/hexane) to give the title compound (195 mg, 84%) as a colorless oil.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (solvent gradient; 0→15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7b0fb1577fde40b2b891cb4835428a1d
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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