Ammonium Acetate → HCID 19379391, compound

Participants

Reaction Steps

A 13% solution of titanium trichloride in 20% hydrochloric acid (173 ml) was added to a degassed solution of ammonium acetate (100 g) in methanol (300 ml) at 0° C. under nitrogen over 20 min. A solution of sodium methoxide (1.49 g) in methanol (60 ml) was added to a suspension of 5-nitro-2-oxo-6-thienylpiperidine (5 g, Example 25a) in methanol (75 ml) and the mixture stirred for 20 min. This solution was then added dropwise to the titanium trichloride/buffer solution at 0° C. under nitrogen. The reaction was stirred at 0° C. for 30 min and at 23° C. for 30 min. Methanol was removed in vacuo and ethyl acetate was added to the residue. The emulsion was filtered through Hi-flo and then shaken with brine. The organic phase was dried (MgSO4) and concentrated in vacuo. The material was chromatographed on silica using (1:1 then 9:1) ethyl acetate in petroleum ether (60-80) as eluant to give 2,5-dioxo-6-thienylpiperidine. m/z (CI+) m/z 105 (MH, 53%).

Provenance & Evidence