Reacción #1918170

Ecuación de reacción

193

(11S,11aS)-8-Methyl-7,9-dimethoxy-11-hydroxy-10-N-(2′,2′,2′-tri-chloroethoxylcarbonyl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

→

product ( 194 )

Rendimiento 94.4%

8-Methyl-7,9-dimethoxy-1,2,3,11a-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-5-one

Rendimiento 94.4%

Disolventes

EtOAc

THF

—

NH4OAc

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe solution was dried over anhydrous MgSO4
2. 2
   Filtraciónthe solids were filtered
3. 3
   Lavadorinsed with EtOAc (50 mL)
4. 4
   OtroRemoval of excess solvent

Procedimiento

10% Cd/Pb couple (1.34 g; 10.7 mmol Cd) was added to a rapidly stirring solution of 193 (1 g; 2.14 mmol) in a mixture of THF (15 mL) and 1 N NH4OAc (15 mL). After 3.5 hours the reaction was diluted with EtOAc (150 mL). The solution was dried over anhydrous MgSO4 and the solids were filtered and rinsed with EtOAc (50 mL). Removal of excess solvent yielded the product (194) as a white glass (554 mg, 2.021 mmol, 94%). 1H NMR (270 MHz, CDCl3) (mixture of imine and methyl ether forms) δ7.72 (imine, d, J=4.39, 1H), 7.29 (s, 1H), 3.90 (s, 3H), 3.88-3.51 (m, 3H+2H+1H), 2.37-2.04 (m, 4H), 2.22 (s, 3H); 13C NMR (67.8 MHz, CDCl3) δ164.65, 161.41, 156.79, 153.47, 133.87, 126.29, 124.27, 105.71, 60.98, 55.80, 55.70, 53.71, 46.70, 29.52, 29.34, 24.13, 9.33.

Fuente