Реакция #448745

Уравнение реакции

hydrogen chloride methanol

9-(4-nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta(e][1,4]diazepin-10(1H)-one

bromocresol green

sodium cyanoborohydride

→

title compound

Выход 70.1%

(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Выход 70.1%

Растворители

water

methanol

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Экстракцияextracted with 3 portions of ethyl acetate
2. 2
   ПромывкаThe pooled organic layer was washed serially with water and saturated aqueous NaCl solution
3. 3
   Сушкаdried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)
7. 7
   Другоеcrystallized from ethyl acetate-diethyl ether

Методика

To a suspension of 9-(4-nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta(e][1,4]diazepin-10(1H)-one (10.2 g, 30 mmol) and bromocresol green in a mixture of methanol (100 mL)-tetrahydrofuran (THF) (30 mL) was added sodium cyanoborohydride (2.08 g, 33 mmol). To this mixture, 10% hydrogen chloride/methanol was slowly added dropwise at the same temperature until the color of the reaction mixture had ceased to change. This reaction mixture was diluted with water and extracted with 3 portions of ethyl acetate. The pooled organic layer was washed serially with water and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1) and crystallized from ethyl acetate-diethyl ether to provide 7.09 g (yield 70%) of the title compound. m.p. 154°-155° C.

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