Water → {1-Azabicyclo[3.2.1]octan-5-yl}methanol

HRID 5362

Reaktionsgleichung

Reaktionsgleichung von HRID 5362
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C([O:14][C:15]([C:17]12[CH2:24][N:21]([CH2:22][CH2:23]1)[CH2:20][CH2:19][CH2:18]2)=O)C.O.[OH-].[Na+]>O1CCCC1>[N:21]12[CH2:24][C:17]([CH2:15][OH:14])([CH2:23][CH2:22]1)[CH2:18][CH2:19][CH2:20]2

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15663615Ethyl 1-azabicyclo[3.2.1]octane-5-carboxylateHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 19795992{1-Azabicyclo[3.2.1]octan-5-yl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

Aufarbeitung

  1. temperaturerefluxed for one hour
  2. temperaturecooled (0° C.)
  3. filtrationthe mixture was filtered through Celite (the solid
  4. washwas washed with tetrahydrofuran) and
  5. concentrationconcentrated in vacuo
  6. customto afford 6.50 g (92%) of viscous, colorless oil, which
  7. temperatureon cooling

Quellen und Nachweise

ORD-Eintrag
ord-3f6f7292f4214dacbbc44e42e9963d38
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244907

Verknüpfte Notizen

Wird geladen…