反应详情

温度

50 °C

A suspension of NaH (0.066 g, 0.0028 mol) in THF (25 mL) was treated with 1-t-butylcarbamoyl-3-hydroxypyrrolidine (Ref. Syn. Commun. 15, 587.) (0.5 g, 0.0027 mol) and the reaction warmed to 50° C. for 30 min. After cooling to ambient temperature, 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (0.55 g, 0.0027 mol) in THF (5 mL) was added and the reaction heated to reflux for 2.5 h. The solvent was evaporated, the residue treated with ice-water, and the mixture extracted with ether. The extracts were washed with brine, dried, and the solvent evaporated. The residue was dissolved in ether (50 mL) and treated with a slow stream of HCl for 5 min. After stirring overnight, the reaction was extracted with cold water. The aqueous was washed with ether, made basic, and extracted with EtOAc. The extracts were washed with brine, dried, and the solvent evaporated to give a clear oil. The HCl salt (0.42 g) crystallized from EtOAc, m.p. 127°-128° C. (Compound 27).

1. temperatureAfter cooling to ambient temperature
2. temperaturethe reaction heated
3. temperatureto reflux for 2.5 h
4. customThe solvent was evaporated
5. additionthe residue treated with ice-water
6. extractionthe mixture extracted with ether
7. washThe extracts were washed with brine
8. customdried
9. customthe solvent evaporated
10. dissolutionThe residue was dissolved in ether (50 mL)
11. additiontreated with a slow stream of HCl for 5 min
12. extractionthe reaction was extracted with cold water
13. washThe aqueous was washed with ether
14. extractionextracted with EtOAc
15. washThe extracts were washed with brine
16. customdried
17. customthe solvent evaporated
18. customto give a clear oil
19. customThe HCl salt (0.42 g) crystallized from EtOAc, m.p. 127°-128° C. (Compound 27)