Reacción #509116

Ecuación de reacción

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

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

KOtBu

→

product

Rendimiento 97.0%

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

Rendimiento 97.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting solution was stirred at RT overnight
2. 2
   Otrobefore being quenched by addition of HCl (1N)
3. 3
   Extracciónextracted into EtOAc
4. 4
   LavadoThe combined organic layers were washed with sat. aq. NaHCO3 and brine
5. 5
   Secadobefore being dried (Na2SO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe crude material was purified by FC (PE/EtOAc 85:15)

Procedimiento

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)+.

Fuente