ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate → (4R,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one

HRID 1173620노트

반응식

HRID 1173620 반응식
C(OC([NH:11][C@@H:12]([CH2:28][CH3:29])[CH:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:14][C:15](OCC)=[O:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Si:21]([O:20][C@H:13]1[C@H:12]([CH2:28][CH3:29])[NH:11][C:15](=[O:16])[CH2:14]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].[Si:21]([O:20][C@@H:13]1[C@H:12]([CH2:28][CH3:29])[NH:11][C:15](=[O:16])[CH2:14]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

참가 물질

5

반응물 1

HCID 67105077ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate

생성물 2

HCID 59557019(4R,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one수율 59%HCID 67105254(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one수율 13%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

실험 절차

To a solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate (64.0 g) in methanol (500 mL) was added 10% palladium carbon (containing 50% water, 6.5 g), and the mixture was stirred at room temperature for 3.5 hr under a hydrogen atmosphere and filtered. Sodium methoxide (13.6 g) was added to the filtrate, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1→1/4) to give the title compound (yield: 21.6 g, 59%) and (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one (yield: 4.64 g, 13%) as a colorless solid and a colorless oil, respectively.

후처리

  1. filtrationfiltered
  2. additionSodium methoxide (13.6 g) was added to the filtrate
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. additionWater was added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1→1/4)

출처 및 근거

ORD 기록
ord-75ad5d3a6cc34b98a6e3650b45272d31
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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