Sodium Hydroxide → 2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-ol

HRID 4977

反応式

HRID 4977 の反応式
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[CH:8]2[C:13](=[O:14])[CH:12]3[CH2:15][N:9]2[CH2:10][CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[C:17]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:16])[CH:8]2[CH:13]([OH:14])[CH:12]3[CH2:15][N:9]2[CH2:10][CH2:11]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 197974272-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 197974612-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-(Diphenylhydroxymethyl)-1-azabicyclo[2.2.1]heptan-3-one (210 mg) was dissolved in THF (5 ml) at -78° C. under argon. Lithium aluminium hydride (3 ml, 1.0M in ether) was added and the mixture stirred at -78° C. for 30 min, and then warmed to room temperature whereupon the reaction mixture became homogeneous. Water (0.1 ml) was added followed by sodium hydroxide (0.35 ml, 3N) and water (0.35 ml) affording a granular precipitate. Solid sodium sulphate was added, the mixture was filtered and the filtrate evaporated. The resulting diol was used without further purification.

後処理

  1. temperaturewarmed to room temperature whereupon the reaction mixture
  2. customaffording a granular precipitate
  3. filtrationthe mixture was filtered
  4. customthe filtrate evaporated
  5. customThe resulting diol was used without further purification

出典と根拠

ORDレコード
ord-2296a711d5b9416e8708573c01ee1a3d
出典データセット
uspto-grants-1993_09
特許番号
US05242930

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