반응 #45099

반응 방정식

tert-butyl piperazine-1-carboxylate

[(1-ethoxycyclopropyl)oxy]trimethylsilane

acetic acid

sodium cyanoborohydride

→

tert-butyl 4-cyclopropylpiperazine-1-carboxylate

수율 68.3%

용매

tetrahydrofuran

methanol

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   여과filtered
3. 3
   기타evaporated to dryness
4. 4
   workup.ADDITION1N HCl (40 ml) and water (60 ml) were added
5. 5
   추출the solution extracted with ethyl acetate (3×50 ml)
6. 6
   추출extracted with ethyl acetate (4×50 ml)
7. 7
   세척The organic extracts were washed with saturated sodium chloride solution (50 ml)
8. 8
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    기타evaporated to dryness

실험 절차

A solution of tert-butyl piperazine-1-carboxylate (9.31 g, 50 mmol), [(1-ethoxycyclopropyl)oxy]trimethylsilane (20.11 mL, 100.00 mmol) and acetic acid(14.31 mL, 250.00 mmol) in tetrahydrofuran (100 mL), methanol (10 mL) was treated with sodium cyanoborohydride (4.71 g, 75.00 mmol) at 20° C. The resulting solution was stirred at 60° C. for 18 h. The reaction mixture was cooled, filtered and evaporated to dryness. 1N HCl (40 ml) and water (60 ml) were added and the solution extracted with ethyl acetate (3×50 ml). The aqueous layer was basified to pH 10 with solid potassium carbonate and extracted with ethyl acetate (4×50 ml). The organic extracts were washed with saturated sodium chloride solution (50 ml) and dried over MgSO4, filtered and evaporated to dryness to give tert-butyl 4-cyclopropylpiperazine-1-carboxylate (7.73 g, 68.3%) as a white waxy solid.

출처