反应详情

To a stirring solution of 4-[1-hydroxy-5-(2-methylthiopyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid benzyl ester (9.5 g. crude, 0.0146 mole) in methanol (130 mL) at 20° C. was added titanium (III) chloride (25 mL, 0.029 mole, 15% wt in 20-30% HCl) dropwise over 10 minutes. The reaction was allowed to stir for 3 hours then quenched by pouring slowly into a mixture of 10% aqueous sodium bicarbonate (1.5 L) and ethyl acetate (600 mL). After stirring for 30 minutes the organic layer was removed and aqueous extract washed with ethyl acetate (2×200 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, and concentrated to an oil. The oil was chromatographed on silica using 60% ethyl acetate/hexane to give 6.35 g of a yellow foam upon concentration of product containing fractions.

1. customthen quenched
2. additionby pouring slowly into a mixture of 10% aqueous sodium bicarbonate (1.5 L) and ethyl acetate (600 mL)
3. stirringAfter stirring for 30 minutes the organic layer
4. customwas removed
5. extractionaqueous extract
6. washwashed with ethyl acetate (2×200 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated to an oil
9. customThe oil was chromatographed on silica using 60% ethyl acetate/hexane