Reaktion #73468

Reaktionsgleichung

HCl

(1S,2S,4S)-5-Oxo-2-phenyl-bicyclo[2.2.1]heptane-2-carbonitrile

NaBH4

NaCl

→

( 87 )

Ausbeute 98.1%

(1S,2S,4S)-5-Hydroxy-2-phenyl-bicyclo[2.2.1]heptane-2-carbonitrile

Ausbeute 98.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at −70° C
2. 2
   ExtraktionThe mixture was extracted three times
3. 3
   TrocknenThe organic layer was dried over MgSO4
4. 4
   Sonstigeevaporated

Vorschrift

0.9 g (4.3 mmol) of (1S,2S,4S)-5-Oxo-2-phenyl-bicyclo[2.2.1]heptane-2-carbonitrile (86) were dissolved using 20 mL of ethanol and 161 mg (4.3 mmol) of NaBH4 was added at −70° C. The mixture was stirred at ambient temperature for 1 h, 100 mL of a saturated aqueous NaCl-solution was added and the pH adjusted to 2-3 using aqueous HCl-solution. The mixture was extracted three times using 50 mL of ethyl acetate each. The organic layer was dried over MgSO4 and evaporated to yield 0.9 g of (87) as a single diastereomer as a colourless oil. Rt=0.76 min (Method 18). Detected mass: 214.1 (M+H+)

Quelle