Sodium Carbonate → HCID 25257234, compound

Participants

Reaction Conditions

Reaction Steps

(also known as 4-oxo-2,6-di-phenanthren-9-yl-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a; 3,4-a′]dinaphthalen-4-ol) (44.5 mg, 0.06 mmoL, 3 mol %), was added a solution made from 2-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-5-(3-(trifluoromethoxy)phenyl)quinoline (1.02 g, 2.12 mmoL) and toluene (3.61 g). The resulting slurry was stirred, heated to 58° C. and then stirred at 58° C. for 8 hours. The resulting mixture was then cooled to room temperature. (1S)-(+)-10-camphorsulfonic acid (148 mg, 0.30 eq) and additional diludine (160 mg, 0.3 eq.) were added and the resulting slurry was stirred at room temperature for 6 hours. To the resulting reaction mixture were added ethyl acetate (4 mL) and aqueous 2N Na2CO3 (6 mL). The phases of the resulting biphasic mixture wre separated. After the clear lower aqueous layer was mostly removed, the remaining organic phase and some precipitates were filtered and the filtrate was washed with 4N HCl for (3-5 times, 6 mL each time), followed by washing with 50% saturated aqueous Na2CO3 solution (2×). The resulting mixture was concentrated to yield the title compound, (R)-2-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-5-(3-(trifluoromethoxy)phenyl)-1,2,3,4-tetrahydroquinoline, as crude product, as an oil.

Provenance & Evidence