反应详情

Into a room temperature, stirred solution of (S)-2-(4-hydroxybutyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.344 g, 0.95 mmol), and MeI (0.179 mL, 2.87 mmol) in DMF (5 mL) add NaH (0.042 g, 1.05 mmol, 20% in mineral oil). Stir overnight. Dilute the mixture with 75% brine (50 mL) and extract with EtOAc (3×100 mL). Concentrate the organic layers under reduced pressure, dilute with EtOAc (40 mL) and wash with 75% brine (5×25 mL). Dry the organic layer over Na2SO4, and filter. Concentrate the mixture under reduced pressure and purify by silica gel chromatography eluting with 20% to 98% EtOAc in hexanes. Combine the purified fractions, concentrate under reduced pressure and place under vacuum to give the title compound: yellow tar (0.209 g), mass spectrum (m/e):373.13 (M+H).

1. extractionextract with EtOAc (3×100 mL)
2. concentrationConcentrate the organic layers under reduced pressure
3. additiondilute with EtOAc (40 mL)
4. washwash with 75% brine (5×25 mL)
5. dry with materialDry the organic layer over Na2SO4
6. filtrationfilter
7. concentrationConcentrate the mixture under reduced pressure
8. custompurify by silica gel chromatography
9. washeluting with 20% to 98% EtOAc in hexanes
10. concentrationCombine the purified fractions, concentrate under reduced pressure and place under vacuum