反応 #509116

反応方程式

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

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

KOtBu

→

product

収率 97.0%

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

収率 97.0%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting solution was stirred at RT overnight
2. 2
   その他before being quenched by addition of HCl (1N)
3. 3
   抽出extracted into EtOAc
4. 4
   洗浄The combined organic layers were washed with sat. aq. NaHCO3 and brine
5. 5
   乾燥before being dried (Na2SO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude material was purified by FC (PE/EtOAc 85:15)

実験手順

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)+.

出典