Methyl iodide → HCID 42635719, compound

Participants

Reaction Conditions

Reaction Steps

2.568 mmol of methyl iodide are added to a suspension of 0.642 mmol of (3S,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-hydroxymethyl-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (example 1a) and 0.963 mmol of NaH (60% dispersion in oil) under argon at 0° C. After stirring for 1 h at 0° C. and 1 h at RT, the reaction mixture is partitioned between TBME and saturated aqueous NaHCO3 solution. The aqueous layer is extracted with TBME (2×)—the combined organic layers are washed successively with H2O and brine, dried with Na2SO4 and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound, which is identified based on the Rf value.

Provenance & Evidence