Methyl iodide → HCID 59278438, compound

Participants

Reaction Steps

To a solution of [(R)-1-(2-bromopyridin-4-yl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (180 mg, 0.57 mmol), methyl iodide (177 μL, 2.84 mmol) and tetrabutylammonium hydrogen sulfate (192 mg, 0.568 mmol) in THF (4.0 mL) is added 50% aqueous sodium hydroxide (2.5 mL). After 1 hour, the reaction mixture is diluted with water (50 mL) and extracted with ethyl ether (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 0-30% EtOAc in heptane to afford [(R)-1-(2-bromopyridin-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester as oil which solidified upon standing.

Provenance & Evidence