(4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one → (R)-4-(2-(1-Ethyl-1H-pyrrol-2-yl)ethyl)-4-methyloxazolidin-2-one
Reaction equation
[CH3:1][C@@:2]1([CH:8]=[CH:9][C:10]2[N:11]([CH2:15][CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1>C(O)C.[Pd]>[CH3:1][C@@:2]1([CH2:8][CH2:9][C:10]2[N:11]([CH2:15][CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1Participants
4
Procedure
To a suspension of 10% palladium-charcoal (50% wet with water) (500 mg) in ethanol (10 ml) was added a solution of (4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one (5.7 g, 25.9 mmol) obtained in Reference example 22 in ethanol (50 ml), and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. After stirring, the palladium-charcoal in the reaction mixture was filtered off using celite, and the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:7) as the eluent to afford the title compound (5.0 g, yield: 87%).
Workup
- stirringAfter stirring
- filtrationthe palladium-charcoal in the reaction mixture was filtered off
- customthe filtrate was evaporated in vacuo
- customThe residue obtained
- customwas purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-2534d8255add46c5855b9f19dbed2bf2
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101650B2
Reaction notes
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