反应详情

温度

0 °C

(S, R)-1-benzyloxycarbonyl-2-(1-hydroxyethyl)-4-tert-butyloxycarbonyl-piperazine (7.6 g) was dissolved in 208 mL of toluene. While stirring, imidazole (3,5 g), triphenylphospine (15.31 g), and Zn(N3)2.pyr2 (14.11 g) were added in that order. The mixture was cooled to 0° C. and diethylazodicarboxylate (10.2 g) was added dropwise. The mixture was warmed to room temperature and stirred for 1 hour, then decanted into a separatory funnel and extracted with 2×360 mL of ethyl acetate. Any solids in the reaction flask were dissolved with 1N HCl, poured into the separatory funnel, and extracted with 2×760 mL of ethyl acetate. The combined organics were washed with 760 mL each of saturated NaHCO3 and brine, dried with Na2SO4, and concentrated. The residue was purified by flash chromatography, eluting with 4:1 hexanes-ethyl acetate to provide 4.19 g of the title compound. Mass spectrum (ESI) 334.1 (M−55).

1. additionpyr2 (14.11 g) were added in that order
2. temperatureThe mixture was warmed to room temperature
3. stirringstirred for 1 hour
4. customdecanted into a separatory funnel
5. extractionextracted with 2×360 mL of ethyl acetate
6. dissolutionAny solids in the reaction flask were dissolved with 1N HCl
7. additionpoured into the separatory funnel
8. extractionextracted with 2×760 mL of ethyl acetate
9. washThe combined organics were washed with 760 mL each of saturated NaHCO3 and brine
10. dry with materialdried with Na2SO4
11. concentrationconcentrated
12. customThe residue was purified by flash chromatography
13. washeluting with 4:1 hexanes-ethyl acetate