Reaktion #1807065

Reaktionsgleichung

sodium borohydride

cis 2-[phenethyl]-5-[(3,4-methylenedioxy)benzoyl]pyrrolidine

ammonium chloride

→

2-[phenethyl]-5-[(3,4-methylenedioxy)-α-hydroxybenzyl]pyrrolidine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evaporated in vacuo
2. 2
   Sonstigeto remove the ethanol
3. 3
   Temperaturthe residue was cooled to 0°
4. 4
   workup.ADDITION50 ml of a saturated sodium carbonate solution was added
5. 5
   ExtraktionThe product was extracted into ethyl acetate
6. 6
   Waschenthe extract was washed with water
7. 7
   Trocknendried over sodium sulfate
8. 8
   Sonstigeevaporated in vacuo
9. 9
   SonstigeThe residue was crystallized from ethyl acetate-hexane

Vorschrift

1.35 g (0.035 mole) of sodium borohydride was added to a stirred solution of 2.70 g (0.0057 mole) of ±cis 2-[phenethyl]-5-[(3,4-methylenedioxy)benzoyl]pyrrolidine in 270 ml ethanol, at 0° temperature. After 1 hour at 0°, the mixture was poured into 100 ml of 10% ammonium chloride solution. The mixture was evaporated in vacuo to remove the ethanol, the residue was cooled to 0°, and 50 ml of a saturated sodium carbonate solution was added. The product was extracted into ethyl acetate, the extract was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate-hexane to give 1.72 g (93%) of the desired ±cis erythro 2-[phenethyl]-5-[(3,4-methylenedioxy)-α-hydroxybenzyl]pyrrolidine (IX), m.p. 122°-123° (dichloromethane-hexane). (Step 7)

Quelle