Potassium Carbonate → Methyl 1-piperidin-1-ylcyclopropanecarboxylate

HRID 386526

反応式

HRID 386526 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 14358246Methyl 1-piperidin-1-ylcyclopropanecarboxylate

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c35e0119cf5c4c44ac7f4b4ee7598f12
出典データセット
uspto-grants-2013_02
特許番号
US08372841B2

関連ノート

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