反应详情

A solution of (S)-1-butyloxycarbonyl-2-pyrrolidinemethanol (1.21, 0.006 mol) in THF (5 mL) was added to a suspension of 60% NaH in oil (0.24 g, 0.006 mol) in THF (30 mL). After 1 h, the mixture was heated to gentle reflux for 1 h. To the solution was added 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1 g, 0.0042 mol) and the reaction heated to reflux overnight. The solvent was evaporated, the residue treated with cold H2O, and the mixture extracted with EtOAc. The extracts were dried and treated with a stream of dry HCl for 3 min. After another hour, the solvent was evaporated, the residue treated with cold H2O, and the mixture extracted with ether. The aqueous fraction was made basic and extracted with EtOAc. The extracts were washed with water, dried, and the solvent evaporated to give a liquid. The HCl salt (0.72 g) crystallized from EtOAc, m.p. 99°-100° C. (Compound 32).

1. temperaturethe mixture was heated
2. temperatureto gentle reflux for 1 h
3. temperaturethe reaction heated
4. temperatureto reflux overnight
5. customThe solvent was evaporated
6. additionthe residue treated with cold H2O
7. extractionthe mixture extracted with EtOAc
8. customThe extracts were dried
9. additiontreated with a stream of dry HCl for 3 min
10. waitAfter another hour
11. customthe solvent was evaporated
12. additionthe residue treated with cold H2O
13. extractionthe mixture extracted with ether
14. extractionextracted with EtOAc
15. washThe extracts were washed with water
16. customdried
17. customthe solvent evaporated
18. customto give a liquid
19. customThe HCl salt (0.72 g) crystallized from EtOAc, m.p. 99°-100° C. (Compound 32)