Heptanoic acid, 7-oxo-, ethyl ester → HCID 131731626, compound

Participants

Reaction Steps

To a solution of rac-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-8-yl acetate ((prepared according to the preparation procedures disclosed in PCT patent application PCT/EP2011/062028, Intermediate HF) (209 mg, 0.560 mmol) in DCE (dry) (10 ml) was added ethyl 7-oxoheptanoate (289 mg, 1.679 mmol) followed by sodium triacetoxy borohydride (356 mg, 1.679 mmol). The mixture was left to stir overnight at room temperature under an atmosphere of nitrogen. The resulting mixture was diluted with water (20 ml) and extracted with EtOAc (3×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was passed through an Isolute® SCX-2 SPE cartridge and was loaded onto a primed (with MeOH 20 ml) SCX-2 cartridge. The methanolic ammonia fractions were concentrated under reduced pressure to afford the titled compound as a mixture with rac-ethyl 7-(8-acetoxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate; The mixture was used in the next step without further purification;

Provenance & Evidence