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

HRID 1020986노트

반응식

HRID 1020986 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][C@:11]([CH2:18][C:19]([CH3:21])=[CH2:20])([C:15]([OH:17])=[O:16])[CH2:10]1.[Si](C=[N+]=[N-])(C)(C)[CH3:23]>CO>[CH3:23][O:16][C:15]([C@@:11]1([CH2:18][C:19]([CH3:21])=[CH2:20])[CH2:12][C:13](=[O:14])[N:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH2:10]1)=[O:17]

참가 물질

4

반응물 2

HCID 167693TrimethylsilyldiazomethaneHCID 58218841(S)-1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid

생성물 1

HCID 58218819(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester수율 105.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (S)-1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid (prepared from c, 430 mg, 1.49 mmol) in MeOH (5 mL) was added TMS-CHN2 (2.24 mL, 4.49 mmol, 2 M solution in hexanes) dropwise. After stirring the yellow colored clear solution at room temperature for 10 min, MeOH was removed under reduced pressure, and the solution was diluted with EtOAc (50 mL) and washed with saturated NaHCO3 solution (25 mL), water (25 mL), brine (25 mL), dried (Na2SO4) and evaporated to obtain (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (474 mg) which was used as such in next step without any further purification. LC-MS: Rt (retention time): 2.14 min, MS: (ES) m/z 302.3 (M+H+).

후처리

  1. customMeOH was removed under reduced pressure
  2. additionthe solution was diluted with EtOAc (50 mL)
  3. washwashed with saturated NaHCO3 solution (25 mL), water (25 mL), brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-c79a1ffd03804b20821a427441512110
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716494B2

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