Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate → (4RS,5RS)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one

HRID 1173561노트

반응식

HRID 1173561 반응식
C(OC([NH:11][CH:12]([CH3:30])[CH:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Si:23]([O:22][CH:13]1[CH:12]([CH3:30])[NH:11][C:15](=[O:16])[C:14]1([CH3:21])[CH3:20])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

참가 물질

4

반응물 1

HCID 59556980Ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate

생성물 1

HCID 67105615(4RS,5RS)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one수율 24%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

실험 절차

To a solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate (2.73 g) in methanol (13 mL) was added 10% palladium carbon (containing 50% water, 170 mg), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere and filtered. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethanol (20 mL). A 20% solution (4 mL) of sodium ethoxide-ethanol was added thereto, and the mixture was refluxed for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/2) to give the title compound (yield: 700 mg, 44%) and (4RS,5RS)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethylpyrrolidin-2-one (yield: 380 mg, 24%), each as an oil.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (20 mL)
  4. additionA 20% solution (4 mL) of sodium ethoxide-ethanol was added
  5. temperaturethe mixture was refluxed for 2 hr
  6. additionWater was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/2)

출처 및 근거

ORD 기록
ord-c0697fa17a3441d79bc9f015aa4d99ba
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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