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

HRID 1917382ノート

反応式

HRID 1917382 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-63c09dcb08bb42f49e95d7b1253e081d
出典データセット
uspto-grants-2013_12
特許番号
US08618094B2

反応ノート

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