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

HRID 1173620ノート

反応式

HRID 1173620 の反応式
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]

参加物

5

反応物 1

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-75ad5d3a6cc34b98a6e3650b45272d31
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

反応ノート

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