Reacción #345148

Ecuación de reacción

potassium sodium tartrate

(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine

diisobutylaluminum hydride

→

(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine

Rendimiento 65.9%

Disolventes

toluene

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe mixture was filtered through Celite
2. 2
   LavadoThe solid was washed with ethyl acetate
3. 3
   Lavadothe combined organic solution was washed with brine
4. 4
   Secadodried over magnesium sulfate
5. 5
   OtroThe solvent was evaporated in vacuo
6. 6
   Otrothe residue was chromatographed on a silica gel column with a mixture of ethyl acetate and n-hexane (1:2-2:1) as an eluent

Procedimiento

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (9.01 g) in toluene (70 ml) was added dropwise 1.5 molar solution of diisobutylaluminum hydride (61.2 m mol) in tetrahydrofuran (40.8 ml) at -78° C. After the mixture was stirred at -78° C. for 1.5 hours, saturated aqueous potassium sodium tartrate was added to the reaction mixture and the mixture was filtered through Celite. The solid was washed with ethyl acetate and the combined organic solution was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of ethyl acetate and n-hexane (1:2-2:1) as an eluent to give (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine (5.51 g) as pale yellow crystal.

Fuente