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

HRID 4977

Reaktionsgleichung

Reaktionsgleichung von HRID 4977
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2296a711d5b9416e8708573c01ee1a3d
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242930

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