Reaktion #167680

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated at 80° C. for 1 hour
2. 2
   Sonstigeto destroy excess borane
3. 3
   TemperaturThe 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
   Sonstigethe water layer was separated
8. 8
   Waschenwashed two times with additional ethyl acetate
9. 9
   SonstigeThe organic layers thus obtained
10. 10
    Einengenconcentrated

Vorschrift

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.

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