tert-butyl (2S)-2-methyl-8-[(1Z)-prop-1-en-1-yl]-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate → tert-butyl (2S)-2-methyl-8-propyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate

HRID 1404990Notes

Reaction equation

HRID 1404990 reaction equation
[CH3:1][C@H:2]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C:5]2[S:16][CH:17]=[C:18](/[CH:19]=[CH:20]\[CH3:21])[C:4]=2[O:3]1>C1COCC1.CO.[Pd]>[CH3:1][C@H:2]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:6][C:5]2[S:16][CH:17]=[C:18]([CH2:19][CH2:20][CH3:21])[C:4]=2[O:3]1

Participants

4

Reactant 1

HCID 86668490tert-butyl (2S)-2-methyl-8-[(1Z)-prop-1-en-1-yl]-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 86668491tert-butyl (2S)-2-methyl-8-propyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2S)-2-methyl-8-[(1Z)-prop-1-en-1-yl]-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (390 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 (366 mg, 93%) 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-b624ec2e9d894094aa199ba4e7cdbc5f
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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