HCID 86648139, compound → HCID 42633209, compound

Participants

Reaction Steps

A solution of 1 mmol of (3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-formyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 12b) and 1.1 mmol of (2-oxo-2-pyrrolidin-1-yl-ethyl)-triphenyl-phosphonium chloride in 5 ml MeOH is added 1.05 mmol of NaOCH3 The reaction mixture is stirred at RT overnight. The reaction mixture is quenched by addition of 0.1 N HCl and H2O. The phases are separated and the organic phase is washed with saturated aqueous NaHCO3 solution and brine. The combined aqueous phases are extracted with TBME. The combined organic layers are dried over Na2SO4 and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and is identified based on the Rf value.

Provenance & Evidence