Реакция #361237

Уравнение реакции

sodium borohydride

7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

→

7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol

Выход 29.1%

Условия реакции

Обработка

1. 1
   workup.WAITto stand overnight at the same temperature
2. 2
   Другоеevaporated in vacuo
3. 3
   workup.ADDITIONThe residue was diluted with water
4. 4
   Экстракцияextracted twice with dichloromethane
5. 5
   ПромывкаThe combined extracts were washed with brine
6. 6
   Сушкаdried over sodium sulfate
7. 7
   workup.ADDITIONtreated with 4N hydrogen chloride in ethyl acetate
8. 8
   Другоеevaporated in vacuo
9. 9
   Фильтрацияfiltered
10. 10
    ДругоеThe filtrate was evaporated in vacuo
11. 11
    workup.ADDITIONdiluted with ammonia aqueous solution
12. 12
    Экстракцияextracted twice with dichloromethane
13. 13
    ПромывкаThe combined extracts were washed with brine
14. 14
    Сушкаdried over sodium sulfate
15. 15
    Другоеchromatographed over silica gel
16. 16
    ДругоеThe eluate was evaporated in vacuo
17. 17
    Промывкаthe residue was washed with diethyl ether

Методика

An aqueous solution (92 ml) of sodium borohydride (18.29 g) was added dropwise to a stirred solution of 7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (25.01 g) at ambient temperature over 20 minutes. The resulting mixture was stirred for 4 hours and allowed to stand overnight at the same temperature and evaporated in vacuo. The residue was diluted with water and extracted twice with dichloromethane. The combined extracts were washed with brine, dried over sodium sulfate, treated with 4N hydrogen chloride in ethyl acetate, and evaporated in vacuo. The residue was suspended in methanol and filtered. The filtrate was evaporated in vacuo, diluted with ammonia aqueous solution, and extracted twice with dichloromethane. The combined extracts were washed with brine, dried over sodium sulfate, and chromatographed over silica gel using dichloromethane-methanol. The eluate was evaporated in vacuo and the residue was washed with diethyl ether to afford 7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (7.33 g) as a dark yellow powder (diastereomers mixture).

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