تفاعل #82172

معادلة التفاعل

(3aS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

nitronium tetrafluoroborate

→

(3aS-cis)-5-ethoxy-1,2,3,3a,8,8a- hexahydro-7-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction was quenched by the addition of ice and saturated sodium bicarbonate solution with vigorous stirring
2. 2
   أخرىThe organic layer was separated
3. 3
   تجفيفdried over anhydrous sodium sulfate
4. 4
   تركيزconcentrated to an oil
5. 5
   أخرىThis was purified by chromatography over silica gel
6. 6
   workup.ADDITIONThe fractions containing the product
7. 7
   تركيزconcentrated to an oil which
8. 8
   أخرىcrystallized from hexane

الإجراء التجريبي

A degassed solution, under nitrogen, of 3.70 g of (3aS-cis)-5-ethoxy-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole in 50 ml of dry chloroform was treated with 2.00 g of nitronium tetrafluoroborate at a reaction temperature of +10°. After 20 minutes, the reaction was quenched by the addition of ice and saturated sodium bicarbonate solution with vigorous stirring. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to an oil. This was purified by chromatography over silica gel using ethyl acetate as the eluent. The fractions containing the product were combined and concentrated to an oil which crystallized from hexane to afford crystals of pure (3aS-cis)-5-ethoxy-1,2,3,3a,8,8a- hexahydro-7-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole, mp 106°-108° C.

المصدر