(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

HRID 1020987노트

반응식

HRID 1020987 반응식
[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]

참가 물질

5

반응물 1

HCID 58218819(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

생성물 1

HCID 58218845(S)-1-(2,6-dimethyl-phenyl)-3-isobutyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester수율 94.5%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  1. customresulting black suspension
  2. filtrationfiltered through celite
  3. washwashed with MeOH (25 mL) and volatiles from filtrate
  4. customwere evaporated
  5. customto obtain crude product which
  6. customwas purified by flash chromatography (SiO2, 20→60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-11c0a1ff412549cba929a11da3ea795c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716494B2

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