357338-44-4 → HCID 15979801, compound

HRID 1924337Notes

Reaction equation

HRID 1924337 reaction equation
[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

Participants

5

Reactant 2

HCID 23531071357338-44-4HCID 53629211HCID 53629211, compound

Product 1

HCID 15979801HCID 15979801, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e881bb617928405780b8f98f7e4ed9c1
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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