Reacción #537021

Ecuación de reacción

(S)-isopropyl 4-((4-chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate

→

solid

Rendimiento 94.0%

(S)-4-((3-Methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

Rendimiento 94.0%

Disolventes

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadded to the reaction mixture, which
2. 2
   Otroat room temperature
3. 3
   Otroovernight
4. 4
   FiltraciónThe catalyst is filtered off
5. 5
   Concentraciónthe solution is concentrated under reduced pressure
6. 6
   Otroto obtain a pale yellow solid
7. 7
   OtroThe solid is triturated with ether twice
8. 8
   Otrodried under high vacuum

Procedimiento

A mixture of (S)-isopropyl 4-((4-chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate (12.53 g, 28.55 mmol) and 10% palladium on carbon (1.00 g) in methanol (150 mL) is hydrogenated at 50 psi at room temperature overnight. A fresh batch of 10% palladium on carbon (1.2 g) is slurried in water (˜2 mL) and added to the reaction mixture, which is hydrogenated (50 psi) at room temperature overnight. The catalyst is filtered off and the solution is concentrated under reduced pressure to obtain a pale yellow solid. The solid is triturated with ether twice and dried under high vacuum to afford a yellow solid (10.80 g, 94%). LC-ES/MS m/z 405.2 [M+H]+

Fuente