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Triethylamine → Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

HRID 1196511
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HRID 1196511 반응식
Cl[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=1.[CH2:13]([N:15](CC)[CH2:16][CH3:17])[CH3:14].N1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:15]1([CH2:2][C:3]2[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=2)[CH2:16][CH2:17][CH2:14][CH2:13]1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 14625089Methyl 2-(chloromethyl)-4-pyridinecarboxylate

생성물 1

HCID 15123252Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of product of stage (iii) (1.6 g) in dry dichloromethane (50 ml) at -50° was treated with triethylamine (1.07 ml) and the mixture was stirred for 5 min. A pre-cooled solution of pyrrolidine (1.28 ml) in dry dichloromethane (30 ml) was added at -60° and the mixture was stirred at -60° to 0° for 1 h and at ambient temperature for 72 h. The mixture was poured into aqueous sodium carbonate (1M; 50 ml) and the product was extracted with dichloromethane (50 ml). The organic solution was dried and evaporated leaving an oily residue (1.7 g) which was purified by flash chromatography eluting with dichloromethane/methanol/ammonia 200:10:1 to give the title compound as an oil (0.3 g).

후처리

  1. stirringthe mixture was stirred at -60° to 0° for 1 h and at ambient temperature for 72 h
  2. extractionthe product was extracted with dichloromethane (50 ml)
  3. customThe organic solution was dried
  4. customevaporated

출처 및 근거

ORD 기록
ord-c292ac9679cd4d149a053af40438d7a2
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05114945

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