5-hydroxy-4-propyldihydrofuran-2(3H)-one → HCID 15979801, 화합물

HRID 2043697노트

반응식

HRID 2043697 반응식
[F:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:11][NH2:12])[CH:8]=[CH:7][CH:6]=[CH:5]2.O[CH:14]1[O:18][C:17](=O)[CH2:16][CH:15]1[CH2:20][CH2:21][CH3:22]>ClCCCl.ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH2:11][N:12]1[CH2:14][CH:15]([CH2:20][CH2:21][CH3:22])[CH2:16][C:17]1=[O:18])[CH:8]=[CH:7][CH:6]=[CH:5]2

참가 물질

5

반응물 2

HCID 235310715-hydroxy-4-propyldihydrofuran-2(3H)-oneHCID 53629211HCID 53629211, 화합물

생성물 1

HCID 15979801HCID 15979801, 화합물수율 20%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-(2-fluoroindolizin-3-yl)methanamine x263 (0.38 g, 2.3 mmol) and 5-hydroxy-4-propyldihydrofuran-2(3H)-one x252 (0.33 g, 2.3 mmol) in DCE (12 ml) is kept at room temperature for 2 h, then STAB (0.74 g, 3.5 mmol) is added, and the mixture is stirred overnight. The reaction mixture is kept under stirring at 50° C. for 2 h, cooled to room temperature, and diluted with dichloromethane (10 ml). The mixture is washed with a 20% K2CO3 solution (2×15 ml), and the aqueous layer is washed with brine (25 ml), dried over anhydrous Na2SO4 and evaporated. The residue (0.60 g) is purified by chromatography on silica gel (gradient: chloroform to chloroform/methanol 50/1) to isolate a product of approximately 80% purity (0.162 g). This product is purified by chromatography on silicagel (hexane/ethyl acetate 5/2) to afford pure 1-[(2-fluoroindolizin-3-yl)methyl]-4-propylpyrrolidin-2-one 264 (0.126 g).

후처리

  1. additionSTAB (0.74 g, 3.5 mmol) is added
  2. stirringunder stirring at 50° C. for 2 h
  3. washThe mixture is washed with a 20% K2CO3 solution (2×15 ml)
  4. washthe aqueous layer is washed with brine (25 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customThe residue (0.60 g) is purified by chromatography on silica gel (gradient: chloroform to chloroform/methanol 50/1)
  8. customto isolate a product of approximately 80% purity (0.162 g)
  9. customThis product is purified by chromatography on silicagel (hexane/ethyl acetate 5/2)

출처 및 근거

ORD 기록
ord-545f5111903e4edfb863a7c0416c7ec9
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586623B2

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