tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy) butyl)cyclopropanecarboxylate → (6S)-7-(tert-butyldimethylsilyloxy)-6-ethyl-5-azaspiro[2.4]heptan-4-one

HRID 1967287ノート

反応式

HRID 1967287 の反応式
C(OC([NH:11][C@@H:12]([CH2:32][CH3:33])[CH:13]([C:22]1([C:25](OC(C)(C)C)=[O:26])[CH2:24][CH2:23]1)[O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Si:15]([O:14][CH:13]1[C:22]2([CH2:24][CH2:23]2)[C:25](=[O:26])[NH:11][C@H:12]1[CH2:32][CH3:33])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

参加物

4

反応物 1

HCID 59556935tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy) butyl)cyclopropanecarboxylate

生成物 1

HCID 58238351(6S)-7-(tert-butyldimethylsilyloxy)-6-ethyl-5-azaspiro[2.4]heptan-4-one収率 60%

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 tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy)butyl)cyclopropanecarboxylate (1.18 g) in methanol (20 mL) was added 10% palladium carbon (150 mg), and the mixture was stirred at room temperature for 18 hr under a hydrogen atmosphere and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in methanol (20 mL). Sodium methoxide (230 mg) was added and the mixture was refluxed for 2.5 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=30/1→1/2) to give the title compound as a colorless oil (yield: 397.8 mg, 60%).

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol (20 mL)
  4. additionSodium methoxide (230 mg) was added
  5. temperaturethe mixture was refluxed for 2.5 hr
  6. additionWater was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/2)

出典と根拠

ORDレコード
ord-3b6494bd174646f18d41310ddaecc82b
出典データセット
uspto-grants-2013_04
特許番号
US08420694B2

反応ノート

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