Methyl Ethyl Ketone → HCID 67220682, compound

Participants

Reaction Steps

To a stirred solution of N-(3-chloro-4-fluorophenyl)-4-[(2R)-morpholin-2-ylmethyl]piperazine-1-carboxamide (300 mg, 0.84 mmol) and 2-butanone (0.16 ml, 1.12 mmol) in THF:DCM, 1:1 (8 ml), was added titanium tetraisopropoxide (1.99 ml, 6.72 mmol) and the reaction stirred at ambient temperature for 3 hours. Sodium tris-acetoxyborohydride (356 mg, 1.68 mmol) was added and the reaction stirred overnight. 2M NaOH was then added and the cloudy mixture filtered through celite. The filtrate was then extracted with EtOAc (×2), organics dried (Na2SO4), filtered and evaporated to a yellow oil. This was then purified by reverse phase HPLC using basic modifier to give the product as a yellow gum (42 mg, 0.11 mmol, 13% yield).

Provenance & Evidence