Methyl bromoacetate → HCID 86601996, compound

HRID 1435887Notes

Reaction equation

HRID 1435887 reaction equation
[CH3:1][S:2][C:3]1[C:8]2[CH:9]=[C:10]3[N:14]([C:7]=2[CH:6]=[CH:5][N:4]=1)[CH2:13][CH2:12][C:11]3=[O:15].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>C1COCC1>[OH:15][C:11]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:10]2[N:14]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[C:8]=3[CH:9]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 57429279HCID 57429279, compound

Product 1

HCID 86601996HCID 86601996, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(methylthio)-6,7-dihydro-8H-pyrido[3,4-b]pyrrolizin-8-one (0.15 g, 0.68 mmol), methyl bromoacetate (0.34 mL), Zn—Cu (0.226 g) in THF (3.0 mL) was sonicated for 2 h. The mixture was then heated at 60° C. for 5 min. until completion of the reaction. The reaction mixture was partitioned between EtOAc and NH4Cl. The organic phase was separated, dried over Na2SO4, filtered and evaporated under reduced pressure to provide the title compound. The compound was purified by flash chromatography.

Workup

  1. customwas sonicated for 2 h
  2. customThe reaction mixture was partitioned between EtOAc and NH4Cl
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f550db041a3a4645bc9ef7b1b8ac3be8
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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