Imidazole → HCID 13812518, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-methyl 2-methylserinate hydrochloride from Step A (14.4 g, 85.0 mmol) and imidazole (19.1 g, 280 mmol) in dry DMF (77 mL) was cooled to 0° C. and treated with tert-butyldimethylsilyl chloride (14.1 g, 93.0 mmol). The mixture was stirred at 0° C. for 25 min, and was then allowed to warm to ambient temperature and stirred for 18 h. Water (500 mL) was added and the mixture extracted with ether (4×150 mL). The combined organic extracts were washed successively with water and brine, dried (anhydrous Na2SO4), filtered and concentrated in vacuo. Purification of the residue by silica gel chromatography, eluting with a gradient of EtOAc:CH2Cl2—0:100 to 100:0, afforded the title compound. MS: m/z=248 (M+1).

Provenance & Evidence