Reacción #567397

Ecuación de reacción

citric acid

sodium borohydride

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde

methylene chloride

→

2

Rendimiento 69.0%

(3aR,4R,5R,6aS)-5-Benzoyloxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Rendimiento 69.0%

Disolventes

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate (3×40 mL)
2. 2
   Lavadothe combined organic layers were washed with water (2×80 mL) and saturated brine (2×80 mL)
3. 3
   Secadodried (magnesium sulfate)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated

Procedimiento

To a suspension of sodium borohydride (650 mg, 17.1 mmol) in methanol (20 mL) at 0° C. (bath temperature) was added a solution of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde (1) (3.5 g, 12.8 mmol) as a solution in 1:1 methanol:methylene chloride (40 mL). After 25 min, saturated citric acid was added cautiously (60 mL), the mixture was extracted with ethyl acetate (3×40 mL), the combined organic layers were washed with water (2×80 mL) and saturated brine (2×80 mL), dried (magnesium sulfate), filtered, and concentrated to afford 2 (2.43 g, 69%).

Fuente