반응 #509116

반응 방정식

3-chloro-2-(chloromethyl)prop-1-ene

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

KOtBu

→

product

수율 97.0%

methyl 14-cyclohexyl-7-methylene-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

수율 97.0%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting solution was stirred at RT overnight
2. 2
   기타before being quenched by addition of HCl (1N)
3. 3
   추출extracted into EtOAc
4. 4
   세척The combined organic layers were washed with sat. aq. NaHCO3 and brine
5. 5
   건조before being dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude material was purified by FC (PE/EtOAc 85:15)

실험 절차

A solution of methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate (prepared as described in International patent application publication WO2006/046030, Example 9)(0.12 M) in DMF was treated with KOtBu (2.1 eq.) in one portion; the resulting mixture was stirred for 30 min at RT then treated dropwise with 3-chloro-2-(chloromethyl)prop-1-ene (1.1 eq.). The resulting solution was stirred at RT overnight before being quenched by addition of HCl (1N) and extracted into EtOAc. The combined organic layers were washed with sat. aq. NaHCO3 and brine, before being dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by FC (PE/EtOAc 85:15) affording the product as a yellow oil (97%). (ES+) m/z 402 (M+H)+.

출처