Trifluoroacetic acid → 4-(Azetidine-1-carbonyl)piperidine

HRID 426084노트

반응식

HRID 426084 반응식
[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[O:6])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1([C:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[O:6])[CH2:2][CH2:3][CH2:4]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 23658779tert-Butyl 4-[(azetidin-1-yl)carbonyl]piperidine-1-carboxylate

생성물 1

HCID 236587804-(Azetidine-1-carbonyl)piperidine수율 102.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl 4-(azetidin-1-ylcarbonyl)piperidine-1-carboxylate (0.50 g, 1.86 mmol) was dissolved in methylene chloride (10 mL) and to the solution was added trifluoroacetic acid (2.12 g, 18.6 mmol). The mixture was stirred at RT overnight and then the solvent was removed by evaporation. The residue was dissolved in a small amount of methanol and THF and the solution was then loaded on a cation exchange sorbent (Isolute® SCX-2; 10 g). The column washed with THF and the product was then eluted with ammonia saturated methanol. The solvent was removed by evaporation. There was obtained 0.32 g (100%) of 4-(azetidin-1-ylcarbonyl)piperidine. 1H NMR (500 MHz, CDCl3): 1.4-1.5 (m, 4H), 2.0-2.2 (m, 3H), 2.4-2.5 (m, 2H), 2.9-3.0 (d, 2H), 3.7-3.8 (t, 2H), 3.9 (s, 1H), 4.0 (t, 2H).

후처리

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in a small amount of methanol and THF
  3. washThe column washed with THF
  4. washthe product was then eluted with ammonia saturated methanol
  5. customThe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-0a8d6dea2fee4d158928244235de5d67
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106208B2

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