Sodium Bicarbonate → E-(6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide

Participants

Reaction Conditions

Reaction Steps

2-[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)-[1,3]dioxan-4-yl]-N-methoxy-N-methyl-acetamide (16.6 g), 2-cyclopropyl-3-formyl-4-(4-fluorophenyl)quinoline (10.0 g), and tetrahydrofuran (400.0 mL) were added to a reactor and then the reaction mixture was cooled to −70° C. A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 36.0 mL) was slowly added to the reaction mixture, the temperature of which was adjusted to −20˜−10° C. The reaction mixture was stirred at the same temperature for 1 hour and then 8% sodium bicarbonate solution (80.0 mL) was added thereto under stirring. The separated organic layer was washed with water (60.0 mL) and then concentrated under reduced pressure to obtain E-(6-{2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-[(4R,6S)-2,2-dimethyl-[1,3]dioxan-4-yl])-N-methoxy-N-methyl-acetamide as a solid (15.6 g, yield 90%).

Provenance & Evidence