Sulfoxonium, trimethyl-, iodide (1:1) → HCID 71602481, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylsulfoxonium iodide [Me3S(O)I] (1.5 eq) and anhydrous THF (12 vol) were charged to a reactor. Cooled to 10˜20° C. and then added t-BuOK (1.5 eq). The resulting mixture was warmed to 60±5° C. and stirred for 1 h. Cooled down back to 10˜20° C. and then dropwise added a solution of (3R,7aS)-6-methylene-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5(1H)-one (1.0 eq) in THF (3 vol) while maintaining the temperature at 60±5° C. The completion of reaction was monitored by HPLC every hour until the conversion >99% (system purity was 55%˜60%). The reaction mixture was then cooled to 15˜20° C., filtered and washed the cake with EtOAc (2 vol). The combined filtrate was washed with brine (3 vol) and the aqueous phase was back-extracted with EtOAc (3 vols). The combined organic phase was concentrated to about 3 vol under vacuum below 45° C. Add silica gel (1 wt/wt) and continued to concentrate to almost dryness. The solid residue was purified by silica gel (2 wt/wt) chromatography eluting with petroleum ether (PE) followed by EtOAc/PE=1:10 (v/v). The yield was about 40% (97.1% HPLC purity). ESI MS m/z (M+H)+ 230.16.

Provenance & Evidence