反応 #82172

反応方程式

(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

溶媒

chloroform

反応条件

後処理

1. 1
   その他the reaction was quenched by the addition of ice and saturated sodium bicarbonate solution with vigorous stirring
2. 2
   その他The organic layer was separated
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated to an oil
5. 5
   その他This was purified by chromatography over silica gel
6. 6
   workup.ADDITIONThe fractions containing the product
7. 7
   濃縮concentrated to an oil which
8. 8
   その他crystallized from hexane

実験手順

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.

出典