反应详情

温度

4 °C

Methanesulphonyl chloride (0.98 ml, 12.6 mmol) was added to a stirred mixture of (1S-cis)-(3-hydroxycyclopentyl)carbamic acid 1,1-dimethylethyl ester (1.41 g, 7.01 mmol) and triethylamine (1.76 ml, 12.6 mmol) in acetone(55 ml) at 4° C. The resulting mixture, containing a white precipitate, was stirred at 4° C. for one hour, then at 21° C. for a further 2.25h, after which it was diluted with water(150 ml) and extracted with ethyl acetate (3×100 ml). The total organic solution was washed with water (50 ml), dried (MgSO4) and evaporated to a white solid. This was dissolved in hot diethyl ether(25 ml) and cooled to 4° C. for 2h, after which time, cyclohexane(25 ml) was added which caused a precipitate to form immediately. The mixture was left to stand at 4° C. for a further 3h, after which the solid was filtered off, washed with cold cyclohexaneldiethyl ether(2:1), then dried to give the title compound (1.202 g) as a white solid, m.p. 88-89° C., [α]D -11.11° (CHCl3 c=0.54%).

1. additionThe resulting mixture, containing a white precipitate
2. extractionextracted with ethyl acetate (3×100 ml)
3. washThe total organic solution was washed with water (50 ml)
4. dry with materialdried (MgSO4)
5. customevaporated to a white solid
6. dissolutionThis was dissolved in hot diethyl ether(25 ml)
7. temperaturecooled to 4° C. for 2h
8. additionafter which time, cyclohexane(25 ml) was added which
9. customto form immediately
10. waitThe mixture was left
11. filtrationafter which the solid was filtered off
12. washwashed with cold cyclohexaneldiethyl ether(2:1)
13. customdried