Potassium Carbonate → Methyl 1-piperidin-1-ylcyclopropanecarboxylate

HRID 386526

반응식

HRID 386526 반응식
[NH2:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[N:1]1([C:2]2([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 123541,5-DiiodopentaneHCID 2735309Methyl 1-aminocyclopropanecarboxylate

생성물 1

HCID 14358246Methyl 1-piperidin-1-ylcyclopropanecarboxylate

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

A mixture of methyl 1-aminocyclopropane-1-carboxylate (0.50 g, 4.35 mmoles), powdered potassium carbonate (2.40 g, 17.4 mmoles), and tetrabutylammonium bromide (0.140 g, 0.43 mmoles) in anhydrous acetonitrile (12 mL) was treated with 1,5-diiodopentane (1.70 g, 5.22 mmoles). The mixture was stirred for three days at 90° C. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified on an Alltech pre-packed silica gel column eluting with ethyl acetate to afford the title compound. MS(DCI) m/z 184 (M+H)+. Vaidyanathan, G.; Wilson, J. W. J. Org. Chem. 1989, 54, 1810-1815.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified on an Alltech pre-packed silica gel column
  5. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-c35e0119cf5c4c44ac7f4b4ee7598f12
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372841B2

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