(1S,2S,4S,5S)-2-((R)-Hydroxy(Quinolin-4-Yl)Methyl)-1-(4-(Trifluoromethyl)Benzyl)-5-Vinylquinuclidin-1-Ium Bromide(WXC02411) synthesis

Yield:101311-12-0 85%

Reaction Conditions:

in tetrahydrofuran;Reflux;

Steps:

Synthesis of catalysts C1-C17

General procedure: The phase-transfer catalysts (C1-C11) were synthesized according to the proceduresbelow. To a solution of cinchonidine (1.00 g, 3.4 mmol) in THF (50 mL) was addedthe aryl benzyl bromides (3.4 mmol). The mixture was heated for 6-8 h at reflux.After cooling to room temperature, the mixture was poured into MTBE (150 mL)under stirring. The precipitated solid was filtrated and recrystallized fromCH3OH/MTBE to afford C1-C11

References:

Li, Ruipeng;Liu, Zhenren;Chen, Liang;Pan, Jing;Zhou, Weicheng [Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 1421 - 1427] Location in patent:supporting information