反应 #586174

反应方程式

KOtBu

tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylate

methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate

CsF

→

product

收率 85.0%

methyl (7R)-7-[(tert-butoxycarbonyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

收率 85.0%

溶剂

DMF

DMF

反应条件

后处理

1. 1
   workup.ADDITIONthen treated
2. 2
   其他over 30 min
3. 3
   workup.STIRRINGThe resulting solution was stirred at RT overnight
4. 4
   其他The reaction mixture was then placed into an ice bath
5. 5
   workup.WAITAfter 1.5 h
6. 6
   其他the reaction was quenched with sat. aq. NH4Cl
7. 7
   萃取extracted into EtOAc
8. 8
   洗涤The combined organic layers were washed with water and brine
9. 9
   干燥before being dried over Na2SO4
10. 10
    过滤filtered
11. 11
    浓缩concentrated in vacuo
12. 12
    其他The crude material was purified by FC (PE/EtOAc 80:20)

实验过程

A solution of methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate (prepared as described in international patent application WO2006/046030) (0.15 M) in DMF was treated with CsF (4 eq) in one portion; the resulting mixture was stirred for 20 min at RT then treated via dropping funnel over 30 min with a solution of tert-butyl (2R)-2-({[(4-nitrophenyl)sulfonyl]oxy}methyl)aziridine-1-carboxylate (1.3 eq) in DMF (0.5 M). The resulting solution was stirred at RT overnight. The reaction mixture was then placed into an ice bath and powdered KOtBu (1.4 eq) added slowly to the reaction mixture. After 1.5 h, the reaction was quenched with sat. aq. NH4Cl and extracted into EtOAc. The combined organic layers were washed with water and brine, before being dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by FC (PE/EtOAc 80:20) affording the product as an off-white foam (85%). (ES+) m/z 505 (M+H)+

来源