Reacción #167680

Ecuación de reacción

solution

tert-butyl 9,10-dichloro-6-oxo-1,2,4a,5,6,7-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepine-3(4H)-carboxylate

borane

Methanol

→

tert-butyl 9,10-dichloro-1,2,4a,5,6,7-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepine-3(4H)-carboxylate

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated at 80° C. for 1 hour
2. 2
   Otroto destroy excess borane
3. 3
   TemperaturaThe reaction was then cooled to room temperature
4. 4
   workup.ADDITION1M HCl was added
5. 5
   workup.ADDITIONAqueous sodium bicarbonate was slowly added to the mixture until the solution
6. 6
   workup.ADDITIONEthyl acetate was then added
7. 7
   Otrothe water layer was separated
8. 8
   Lavadowashed two times with additional ethyl acetate
9. 9
   OtroThe organic layers thus obtained
10. 10
    Concentraciónconcentrated

Procedimiento

To a solution of Example 15B (168 mg, 0.435 mmol) in tetrahydrofuran (1.5 mL) was added borane in tetrahydrofuran (1.74 mL, 1M solution). The resulting mixture was heated to 80° C. overnight. Methanol was then added, and the mixture was heated at 80° C. for 1 hour to destroy excess borane. The reaction was then cooled to room temperature and 1M HCl was added. The mixture was allowed to stir for another 30 minutes. Aqueous sodium bicarbonate was slowly added to the mixture until the solution was basic (pH=8). Ethyl acetate was then added, and the water layer was separated and washed two times with additional ethyl acetate. The organic layers thus obtained were combined and concentrated.

Fuente