Reaktion #341179

Reaktionsgleichung

3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester

Sodium borohydride

→

3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester

Ausbeute 93.6%

Lösungsmittel

dichloromethane

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was evaporated in vacuo
2. 2
   Sonstigeto give clear viscous oil
3. 3
   Waschenwashed with water and brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated

Vorschrift

3-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester (8 g, 35.5 mmol) was dissolved in 100 mL of ethanol. Sodium borohydride (2 g, 53.5 mmol) was added to the solution portionwise at room temperature. After stirring for 3 hours, the reaction was evaporated in vacuo to give clear viscous oil. The oil was dissolved in dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford 7.55 g of 3-hydroxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid, tert-butyl ester as a white crystalline solid; 1H NMR (300 MHz, DMSO-d6): 4.23 (dd, J=2.7, 4.6 Hz, 1H), 4.18-4.06 (m, 2H), 2.17-2.06 (m, 1H), 1.99-1.91 (m, 3H), 1.72-1.50 (m, 5H), 1.47 (s, 9H).

Quelle