반응 #435584

반응 방정식

4-(R)-[1-(tert-butoxycarbonyl)amino-1-cyclobutyl]methyl-1-[1-(R)-phenylethyl]-2-pyrrolidone

→

title compound

수율 84.0%

3-(R)-[1-(tert-Butoxycarbonyl)amino-1-cyclobutyl)methyl-1-[1-(R)-phenylethyl]pyrrolidine

수율 84.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타After removal of the solvent under reduced pressure, 80% water-
2. 2
   workup.ADDITIONcontaining ethanol (15 ml) and triethylamine (3 ml)
3. 3
   workup.ADDITIONwere added to the residue
4. 4
   온도the mixture was heated
5. 5
   온도under reflux for 4 hours
6. 6
   온도After cooling
7. 7
   기타the solvent was removed under reduced pressure and chloroform (30 ml)
8. 8
   workup.ADDITIONwas added to the resulting residue
9. 9
   세척The solution was washed with water (10 ml) and saturated saline (10 ml)
10. 10
    건조dried over anhydrous sodium sulfate
11. 11
    기타After removal of the solvent under reduced pressure

실험 절차

Under a nitrogen atmosphere, 1 mol/l borane-tetrahydrofuran complex solution (5.6 ml) was added dropwise to a tetrahydrofuran solution (15 ml) of 4-(R)-[1-(tert-butoxycarbonyl)amino-1-cyclobutyl]methyl-1-[1-(R)-phenylethyl]-2-pyrrolidone (isomer B1) (700 mg, 1.88 mmol) under ice cooling, followed by stirring at room temperature for 13 hours. After removal of the solvent under reduced pressure, 80% water-containing ethanol (15 ml) and triethylamine (3 ml) were added to the residue and the mixture was heated under reflux for 4 hours. After cooling on standing, the solvent was removed under reduced pressure and chloroform (30 ml) was added to the resulting residue. The solution was washed with water (10 ml) and saturated saline (10 ml) and then, dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the resulting residue was subjected to silica gel column chromatography to obtain the title compound (565 mg, 84%) as colorless crystals from the fraction eluted with chloroform/methanol=20/1.

출처