Reacción #160760

Ecuación de reacción

(+/−)-tert-butyl 6-(tert-butyldimethylsilyloxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

methanol

→

(+/−)-tert-butyl 3-(3-aminopyridin-4-yl)-6-(tert-butyldimethylsilyloxy)cyclohex-2-enylcarbamate

Rendimiento 94.0%

Disolventes

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONby diluting
2. 2
   Filtraciónfiltered
3. 3
   Concentraciónconcentrated the filtrate
4. 4
   workup.ADDITIONTo the crude was added ethyl acetate and saturated NaHCO3
5. 5
   Secadothe organics were dried with sodium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

To a solution of (+/−)-tert-butyl 6-(tert-butyldimethylsilyloxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in AcOH (0.18 M) was added Fe (6.0 equiv.) and the reaction was stirred for 20 h. Worked up by diluting the reaction with methanol, filtered, and concentrated the filtrate. To the crude was added ethyl acetate and saturated NaHCO3, the organics were dried with sodium sulfate and concentrated to give (+/−)-tert-butyl 3-(3-aminopyridin-4-yl)-6-(tert-butyldimethylsilyloxy)cyclohex-2-enylcarbamate as a yellow oil in 94% yield. LCMS (m/z): 420.3 (MH+), LC Rt=3.88 min.

Fuente