Tetrahydro-4H-pyran-4-one → HCID 16038387, compound

Participants

Reaction Steps

6-Chloro-5-fluoro-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D5) (0.286 mmol, 77 mg), Ti(iPrO)4 (2 eq., 0.572 mmol, 0.170 ml), tetrahydro-4H-pyran-4-one (2 eq., 0.572 mmol, 0.053 ml) were stirred together at room temperature for one hour; dry methanol (2 ml) followed by NaBH3CN (2 eq., 0.572 mmol, 36 mgs) were added and the mixture was stirred under argon at room temperature for 3 hours. The crude mixture was subsequently quenched with water (5 ml) and it was firstly purified by SCX followed by chromatography (methanol-NH3-dichloromethane) to yield 6-chloro-5-fluoro-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one, 15 mg, 13%, M++H=353, which was converted into the hydrochloride salt using 1M HCl in diethyl ether.

Provenance & Evidence