反应 #56188

反应方程式

tetrahydrofuran

hydrochloric acid

borane

tetrahydrofuran

tetrahydrofuran

2-benzyl-5-phenyl-1,2,3,4-tetrahydropyrido[4,3-b]indole

→

trans-2-benzyl-2,3,4,4a,5,9b-hexahydro-5-phenyl-1H-pyrido[4,3-b]indole Hydrochloride

溶剂

acetic acid

反应条件

后处理

1. 1
   其他fitted with magnetic stirrer
2. 2
   workup.ADDITIONthermometer, condenser and addition funnel
3. 3
   温度maintained under a nitrogen atmosphere
4. 4
   workup.ADDITIONwas added a solution of 23.9 g
5. 5
   workup.ADDITIONThe addition
6. 6
   温度to maintain the reaction temperature below 9° C
7. 7
   workup.ADDITIONWhen the addition
8. 8
   温度was heated
9. 9
   温度to reflux
10. 10
    温度maintained at this temperature for one hour
11. 11
    其他The solvent was then evaporated in vacuo
12. 12
    其他to afford a white solid mass which
13. 13
    温度The resulting suspension was heated
14. 14
    温度at reflux for one hour
15. 15
    温度cooled
16. 16
    其他Evaporation of tetrahydrofuran and part of the acetic acid
17. 17
    其他resulted in precipitation of a white solid which
18. 18
    其他was separated by filtration
19. 19
    洗涤washed with water
20. 20
    过滤filtered
21. 21
    洗涤washed with ethyl ether and air
22. 22
    其他dried
23. 23
    其他to afford 16.7 g

实验过程

To a solution of 0.140 moles of borane in 150 ml. of tetrahydrofuran stirred at 0° C. in a three-necked round bottom flask fitted with magnetic stirrer, thermometer, condenser and addition funnel, and maintained under a nitrogen atmosphere, was added a solution of 23.9 g. (0.071 mole) of 2-benzyl-5-phenyl-1,2,3,4-tetrahydropyrido[4,3-b]indole in 460 ml. of dry tetrahydrofuran. The addition was carried out at such a rate as to maintain the reaction temperature below 9° C. When the addition was completed the resulting mixture was heated to reflux and maintained at this temperature for one hour. The solvent was then evaporated in vacuo to afford a white solid mass which was suspended in 40 ml. of dry tetrahydrofuran and heated, slowly at first, with 180 ml. of a 1:1 by volume mixture of acetic acid and 5 N hydrochloric acid. The resulting suspension was heated at reflux for one hour, then cooled. Evaporation of tetrahydrofuran and part of the acetic acid resulted in precipitation of a white solid which was separated by filtration and washed with water. The solid was resuspended in tetrahydrofuran, filtered, washed with ethyl ether and air dried to afford 16.7 g. (63%) of the desired trans-isomer. M.P. 256°-260° C.

来源