Reaction #3643

Reaction equation

5-oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

borane dimethylsulfide

methanol

→

4,10-Dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe mixture is refluxed for 6 hours
2. 2
   OtherThe volatiles are removed under vacuum
3. 3
   workup.ADDITIONTo the residue is added 100 ml of 2N NaOH
4. 4
   TemperatureThe mixture is refluxed 5 hours
5. 5
   Filtrationfiltered
6. 6
   ExtractionThe solid is extracted with dichloromethane
7. 7
   Washthe extract is washed with 2N citric acid, water
8. 8
   Dryingdried (Na2SO4)
9. 9
   OtherThe solvent is removed
10. 10
    Otherto give a solid

Procedure

To a suspension of 7.0 g of 5-oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed 5 hours and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed to give a solid.

Source