N-benzylcinchonidinium chloride

Enantioselectivity in acid hydrogenation was not sensitive to the reduction temperature of the catalyst. Modification by N-benzylcinchonidinium chloride substantially deactivated the catalyst and eliminated enantioselectivity. 

N-Benzylcinchonidinium chloride Cinchonanium, 9-hydroxy-l-(phenylmethyl)-, chloride, (9S)- (69221-14-3), 76, 1... 

Crystallise cinchonidine from aqueous EtOH. For the N-benzylcinchonidinium chloride see above entry in this section. [Beilstein 23 III/IV 2824.]... 

Racemic 1,1 -bi-2-naphthol and N-benzylcinchonidinium chloride were purchased from Aldrich Chemical Company, Inc., acetonitrile (LC grade) was obtained from Fisher Scientific. 

These acid washes are to remove residual N-benzylcinchonidinium chloride in the filtrate. 

Efficient enantiomeric separation of the title racemic compound (10a) by complexation with (-i-)-N-benzylcinchonidinium chloride [46], chiral N,N,N-trimethyl-N-(2-hydroxy-l-alkylethyl) ammonium bromide [47] and chiral N-(3-chloro-2-hydro-xypropyl)-N,N,N-trimethylammonium chloride [48] has been reported. However, it was disclosed that chirality of these ammonium salts is not necessary for the enantiomeric separation of 10a, and 10a can easily be separated into enantiomers (10b and 10c) by complexation with racemic or achiral ammonium salts. 

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