Acetic Acid → tert-Butyl 4-cyclopropylpiperazine-1-carboxylate

HRID 16821

반응식

HRID 16821 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(O[C:17]1(O[Si](C)(C)C)[CH2:19][CH2:18]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>O1CCCC1.CO>[CH:17]1([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:19][CH2:18]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 20294524tert-Butyl 4-cyclopropylpiperazine-1-carboxylate수율 68.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

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.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customevaporated to dryness
  4. addition1N HCl (40 ml) and water (60 ml) were added
  5. extractionthe solution extracted with ethyl acetate (3×50 ml)
  6. extractionextracted with ethyl acetate (4×50 ml)
  7. washThe organic extracts were washed with saturated sodium chloride solution (50 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness

출처 및 근거

ORD 기록
ord-96114825bb9d43c79c23579a8e9e0a18
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

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