Reacción #3653

Ecuación de reacción

5,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one

borane dimethylsulfide

methanol

→

desired product

5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is refluxed for 6 hours
2. 2
   OtroThe volatiles are removed under vacuum and to the residue
3. 3
   workup.ADDITIONis added 100 ml of 2N sodium hydroxide
4. 4
   TemperaturaThe mixture is refluxed for 5 hours
5. 5
   Temperaturachilled
6. 6
   Extracciónextracted with dichloromethane
7. 7
   LavadoThe extract is washed with 2N citric acid, water
8. 8
   Secadodried (Na2SO4)
9. 9
   OtroThe solvent is removed under vacuum
10. 10
    Otroto give a solid
11. 11
    OtroThe solid is purified by chromatography on silica gel

Procedimiento

A mixture of 7.0 g of 5,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one in 25 ml of tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours, cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum and to the residue is added 100 ml of 2N sodium hydroxide. The mixture is refluxed for 5 hours, chilled and extracted with dichloromethane. The extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed under vacuum to give a solid. The solid is purified by chromatography on silica gel to give the desired product.

Fuente