Reacción #160768

Ecuación de reacción

(+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl acetate

→

(+/−)-4-(3-aminopyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate

Rendimiento 59.0%

Disolventes

MeOH

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónUpon completion, the solution was filtered through a pad of Celite
2. 2
   Lavadothe pad was washed with ethyl acetate
3. 3
   Concentraciónthe filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe crude was dissolved in ethyl acetate (˜20%)
5. 5
   Temperaturahexanes and heated until all dissolved
6. 6
   workup.WAITto sit at room temperature for 2 days
7. 7
   OtroThe precipitate was then collected

Procedimiento

To a degassed solution of (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl acetate (1.0 equiv.) in MeOH and EtOAc (1:1, 0.1M) was added Pd/C (0.1 equiv.) and the reaction was stirred at room temperature under a hydrogen balloon for 3 days. Upon completion, the solution was filtered through a pad of Celite, the pad was washed with ethyl acetate and the filtrate was concentrated. The crude material contained about 10% of the undesired isomer. The crude was dissolved in ethyl acetate (˜20%) and hexanes and heated until all dissolved. The solution was allowed to sit at room temperature for 2 days. The precipitate was then collected to give (+/−)-4-(3-aminopyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate as the pure product in 59% yield. LC/MS=364.3 (M+H), Rt=0.63 min.

Fuente