Reacción #1880943

Ecuación de reacción

cinchonidine

4-n-Propyl-cyclohexanecarboxylic 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-propyl-1-cyclohexanecarboxylate

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 10 was performed as Example 1 except for substitution of 2.7 g of cinchonidine, 1.5 g of 4-n-Propyl-cyclohexanecarboxylic acid, 2.1 g of N,N′-Dicyclohexyl carbodimide (DCC), 1.2 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-propyl-1-cyclohexanecarboxylate, as a white solid with a chemical purity 91.31%. The optical properties of the resulting compound were tested as in Example 1. The compound exhibited a specific rotation [α] of +5.52 and a helical pitch P of 3.1 μm, with helical twisting power of 32.2 μm−1.

Fuente