HCID 59577095, compound → HCID 59577325, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-(4-(3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-carbonyl)phenyl)ethanone (0.14 g, 0.37 mmol) in diethyl ether (2.0 mL) was added methyl magnesium iodide (0.25 mL, 3.0 M in diethyl ether, 0.75 mmol) dropwise at room temperature. The resulting reaction mixture was heated to reflux for 1.5 h. After this reaction mixture was cooled to 0° C., diluted with diethyl ether, quenched with 1 N hydrochloric acid (2 ml) and the reaction mixture was stirred until the solids disappeared. The organic layer was separated and washed with water (2×2.0 mL), dried (Na2SO4), filtered and the filtrate was directly purified by flash column chromatography (silica gel, 50:50 ethyl acetate/heptane) to provide (3-(2-tert-butyl-4-fluorophenoxy)azetidine-1-yl)(4-(2-hydroxypropan-2-yl)phenyl)methanone (0.081 g, 57%) as a white solid.

Provenance & Evidence