Reacción #66735

Ecuación de reacción

sodium borohydride

sodium borohydride

(9-oxo-3-thia-bicyclo[3.3.1]non-7-yl)-carbamic acid benzyl ester

(9-Oxo-3-thia-bicyclo[3.3.1]non-7-yl)-carbamic acid benzyl ester

sodium borohydride

→

carbamic acid benzyl ester

Rendimiento 40.6%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 4 hours
3. 3
   ConcentraciónThe mixture was then concentrated under reduced pressure and cold water
4. 4
   workup.ADDITIONwas added to the residue as well as dichloromethane
5. 5
   ExtracciónAfter a extraction of the aqueous phase with dichlormethane
6. 6
   Secadothe combined organic layer was dried over anhydrous sodium sulphate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe crude product was purified by silica gel chromatography (cyclohexane:ethyl acetate 40:60)

Procedimiento

To a solution of (9-oxo-3-thia-bicyclo[3.3.1]non-7-yl)-carbamic acid benzyl ester (16, 4.2 g, 13.7 mmol) in ethanol (172 ml) was added sodium borohydride (0.78 g, 20.6 mmol) portionwise at room temperature. The solution was stirred for 1 hour before addition of sodium borohydride (0.2 g, 5 mmol). The reaction mixture was stirred for 2 days, a further portion of sodium borohydride (0.340 g, 9 mmol) was added, and stirring was continued for 4 hours. The mixture was then concentrated under reduced pressure and cold water was added to the residue as well as dichloromethane. After a extraction of the aqueous phase with dichlormethane, the combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (cyclohexane:ethyl acetate 40:60) to yield 9-hydroxy-3-thia-bicyclo[3.3.1]non-7-yl)-carbamic acid benzyl ester as a white solid (0.84 g).

Fuente