反应详情

A solution of 4-carboxymethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 1, 255 mg, 0.952 mmol) and triethylamine (138 μl, 0.982 mmol) in toluene was cooled to 0° C. and isobutylchloroformate (127 μl, 0.982 mmol) added. After stirring at rt for 45 min 4-pyridinecarboximidic acid hydrazide (100 mg, 0.82 mmol) and 3 Å powdered molecular sieves (0.82 g) were added and the reaction heated under reflux for 18 h. On cooling, the mixture was filtered through celite, the filtrate evaporated and the residue dissolved in EtOAc (50 ml). After washing with saturated aqueous Na2CO3 (10 ml) and brine (10 ml), the solvent was removed and the residue purified by flash chromatography (EtOAc then 5% MeOH in EtOAc) to afford the title compound: RT=2.81 min; m/z (ES+)=360.1 [M+H]+.

1. additionwere added
2. temperaturethe reaction heated
3. temperatureunder reflux for 18 h
4. temperatureOn cooling
5. filtrationthe mixture was filtered through celite
6. customthe filtrate evaporated
7. dissolutionthe residue dissolved in EtOAc (50 ml)
8. washAfter washing with saturated aqueous Na2CO3 (10 ml) and brine (10 ml)
9. customthe solvent was removed
10. customthe residue purified by flash chromatography (EtOAc