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

HRID 4977

반응식

HRID 4977 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2296a711d5b9416e8708573c01ee1a3d
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242930

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