Reacción #1880942

Ecuación de reacción

cinchonidine

4-n-hexyloxy-benzoic acid

N,N′-Dicyclohexyl carbodimide

→

(R)-1-(4-quinolyl)-1-[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methyl 4-(hexyloxy)benzoate

Rendimiento 72.3%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónAfter filtering
2. 2
   Otrocondensing
3. 3
   Otrothe residue was subjected to recrystallization from methanol

Procedimiento

Example 9 was performed as Example 1 except for substitution of 2.91 g of cinchonidine, 2.0 g of 4-n-hexyloxy-benzoic acid, 2.33 g of N,N′-Dicyclohexyl carbodimide (DCC), 1.32 g of N,N-(dimethyl amino)-pyridine (DMAP) and 80 ml of dichloromethane into a round-bottom flask. After filtering and condensing, the residue was subjected to recrystallization from methanol, giving (R)-1-(4-quinolyl)-1-[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methyl 4-(hexyloxy)benzoate, as a white solid having a melting point about 70° C. in a 72.3% yield. The optical properties of the resulting compound were tested as in Example 1. The compound exhibited a specific rotation [α] of +57.59 and a helical pitch P of 5.1 μm, with helical twisting power of 19.7 μm−1.

Fuente