2,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dione → Methyl 2-pyrrolidin-2-ylideneacetate

HRID 901332노트

반응식

HRID 901332 반응식
O(C)[Na].C[C:5]1(C)OC(=O)[C:8](=[C:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)[C:7](=[O:17])[O:6]1>CO>[CH3:5][O:6][C:7](=[O:17])[CH:8]=[C:12]1[CH2:16][CH2:15][CH2:14][NH:13]1

참가 물질

4

반응물 2

HCID 7085372,2-Dimethyl-5-(pyrrolidin-2-ylidene)-1,3-dioxane-4,6-dioneHCID 178418582HCID 178418582, 화합물

생성물 1

HCID 69255134Methyl 2-pyrrolidin-2-ylideneacetate수율 85.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a flask containing NaOCH3 (1.21 g, 21.3 mmol) and dry MeOH (50 mL) under nitrogen is added 2,2-dimethyl-5-pyrrolidin-2-ylidene-[1,3]dioxane-4,6-dione (4.5 g, 21.3 mmol) and the contents are refluxed overnight. The reaction is concentrated and the residue is diluted with H20 (50 mL). 1 N HCl is added to obtain a pH of 6 and the mixture is extracted with CHCl3 (3×30 mL). The organic fractions are combined, dried over MgSO4 and concentrated. The crude product is purified by flash chromatography (50% EtOAc/hexanes) to give the title cormpouiid as a white solid (2.57 g, 18.2 mmol). 1H NMR (CDCl3, 300 MHz) 4.49(br. s, 1H), 3.63(s, 3H), 3.62-3.46(m, 2H), 1.75-1.50(m, 2H), 2.11-1.90(m, 2H).

후처리

  1. temperaturethe contents are refluxed overnight
  2. concentrationThe reaction is concentrated
  3. additionthe residue is diluted with H20 (50 mL)
  4. addition1 N HCl is added
  5. customto obtain a pH of 6
  6. extractionthe mixture is extracted with CHCl3 (3×30 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude product is purified by flash chromatography (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ea8971745330461fb90efc9361c2a769
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361663B2

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