Acetic Acid → Tert-butyl 4-cyclobutylpiperazine-1-carboxylate

HRID 16824

반응식

HRID 16824 반응식
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C([BH3-])#N.[Na+]>C1COCC1.O>[CH:1]1([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)[CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 57423951Tert-butyl 4-cyclobutylpiperazine-1-carboxylate수율 50.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

Water (0.15 mL), cyclobutanone (1 g, 14.27 mmol) and acetic acid (1.742 mL, 30.44 mmol) were added to a stirred solution of tert-butyl piperazine-1-carboxylate (1.772 g, 9.51 mmol) in THF (20 mL) under nitrogen. Sodium cyanoborohydride (0.897 g, 14.27 mmol) was added portion wise over a period of 10 mins. The resulting mixture was stirred at 60° C. for 20 h. The reaction mixture was evaporated to dryness and mixed with water (40 mL) and 1M HCl (15 mL). The solution was washed with EtOAc (2×25 mL), basified with solid K2CO3 and extracted with EtOAc (2×15 mL). The organic layer was washed with saturated brine and dried over MgSO4, filtered and evaporated to afford pure tert-butyl 4-cyclobutylpiperazine-1-carboxylate (1.155 g, 50.5%) as a colourless oil.

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. additionmixed with water (40 mL) and 1M HCl (15 mL)
  3. washThe solution was washed with EtOAc (2×25 mL)
  4. extractionextracted with EtOAc (2×15 mL)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-434fd138f4dd4c9a82375bc7ddcf52ad
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737149B2

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