(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester → (S)-1-(2,6-dimethyl-phenyl)-3-isobutyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C@@:5]1([CH2:19][C:20]([CH3:22])=[CH2:21])[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH2:6]1)=[O:4]>CO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([C@@:5]1([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH2:6]1)=[O:4]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
10% Pd/C (120 mg) was added to a solution of (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step d, 474 mg, 1.57 mmol) in MeOH (5 mL) and resulting black suspension was stirred at room temperature overnight under H2 gas using a balloon. The reaction mixture was then diluted with EtOAc (25 mL) and filtered through celite, washed with MeOH (25 mL) and volatiles from filtrate were evaporated to obtain crude product which was purified by flash chromatography (SiO2, 20→60% EtOAc/hexanes) to obtain (S)-1-(2,6-dimethyl-phenyl)-3-isobutyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (450 mg, 94% yield). LC-MS: Rt (retention time): 2.55 min, MS: (ES) m/z 304.1 (M+H+).
Workup
- customresulting black suspension
- filtrationfiltered through celite
- washwashed with MeOH (25 mL) and volatiles from filtrate
- customwere evaporated
- customto obtain crude product which
- customwas purified by flash chromatography (SiO2, 20→60% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-11c0a1ff412549cba929a11da3ea795c
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716494B2
Reaction notes
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