Sodium Hydroxide → (1S,6S)-1-Amino-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene

HRID 1917382노트

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HRID 1917382 반응식
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[NH2:15][C@:16]12[CH2:24][N:23]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:22](=O)[C@@H:21]1[CH2:20][CH:19]=[CH:18][CH2:17]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:15][C@:16]12[CH2:24][N:23]([C@@H:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH3:26])[CH2:22][C@@H:21]1[CH2:20][CH:19]=[CH:18][CH2:17]2

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 67490766(1S,6R)-1-Amino-7-oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene

생성물 1

HCID 67490762(1S,6S)-1-Amino-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene수율 77.7%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
80 °C

실험 절차

A 65% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (2.87 mL, 9.56 mmol) was added to a solution of (1S,6R)-1-amino-7-oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene (612 mg, 2.39 mmol) in toluene (11.9 mL), and the mixture was stirred at 80° C. for one hour. A 5 mol/L sodium hydroxide solution (15.0 mL) was added to the reaction solution with stirring under ice-cooling, followed by extraction with toluene (30 mL×2). The organic layer was washed with brine (90 ml) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 450 mg of the title compound.

후처리

  1. stirringwith stirring under ice-
  2. temperaturecooling
  3. extractionfollowed by extraction with toluene (30 mL×2)
  4. washThe organic layer was washed with brine (90 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-63c09dcb08bb42f49e95d7b1253e081d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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