5-[2-({[(6-chloropyridin-3-yl)methyl]amino}methyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one → 4-[(6-chloropyridin-3-yl)methyl]-6-methylene-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

HRID 552897Notes

Reaction equation

HRID 552897 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][C:11](=[CH2:24])[CH2:12][CH:13]2[O:17][C:16](=[O:18])[CH:15]=[C:14]2N2CCCC2)=[CH:4][CH:3]=1>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:10][C:11](=[CH2:24])[CH2:12][CH:13]3[O:17][C:16](=[O:18])[CH:15]=[C:14]23)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 866324425-[2-({[(6-chloropyridin-3-yl)methyl]amino}methyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one

Product 1

HCID 577798304-[(6-chloropyridin-3-yl)methyl]-6-methylene-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-oneYield 94.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At 100° C., 540 mg (1.55 mmol) of 5-[2-({[(6-chloropyridin-3-yl)methyl]amino}methyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one (III-1) in 20 ml of acetic acid are stirred for 2 hours. The reaction mixture is concentrated under reduced pressure, the residue is taken up in dichloromethane and the mixture is washed with water. The aqueous phase is extracted twice with dichloromethane. The combined organic phase is washed with 1N aqueous sodium hydroxide solution, and the aqueous phase (sodium hydroxide solution) for its part is extracted twice with dichloromethane. The combined organic phase is dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by reciystallization from ethyl acetate gives 407 mg (94% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-6-methylene-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. washthe mixture is washed with water
  3. extractionThe aqueous phase is extracted twice with dichloromethane
  4. washThe combined organic phase is washed with 1N aqueous sodium hydroxide solution
  5. extractionthe aqueous phase (sodium hydroxide solution) for its part is extracted twice with dichloromethane
  6. dry with materialThe combined organic phase is dried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customPurification of the residue by reciystallization from ethyl acetate

Sources & evidence

ORD record
ord-3954fd6a6984437b959d9ecf44519d51
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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