4-Methylmorpholine → HCID 57486381, compound

HRID 403619Notes

Reaction equation

HRID 403619 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[CH:10]=[C:9]([C:12](O)=[O:13])[CH:8]=[CH:7]2)#[N:2].CC(C)CC(Cl)=O.CN1CCOCC1>O1CCCC1>[OH:13][CH2:12][C:9]1[CH:8]=[CH:7][N:6]2[C:11]([CH:10]=1)=[C:3]([C:1]#[N:2])[CH:4]=[CH:5]2

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 66054Isovaleryl chlorideHCID 57486366HCID 57486366, compound

Product 1

HCID 57486381HCID 57486381, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-cyanoindolizine-7-carboxylic acid (0.20 g) in tetrahydrofuran (4.0 mL) were added 3-methylbutyrylchloride (0.16 g) and 4-methylmorpholine (0.13 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The insoluble material was removed from the reaction mixture by filtration. To the filtrate was added ethanol (4.0 mL) and sodium borohydride (0.20 g) was added under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (5.0 mL), and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=30/70-100/0) to give the title compound (0.050 g).

Workup

  1. temperaturecooling
  2. customThe insoluble material was removed from the reaction mixture by filtration
  3. additionTo the filtrate was added ethanol (4.0 mL) and sodium borohydride (0.20 g)
  4. additionwas added under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred at room temperature overnight
  7. additionTo the reaction mixture was added 2 mol/L hydrochloric acid (5.0 mL)
  8. extractionthe resulting mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=30/70-100/0)

Sources & evidence

ORD record
ord-25458be1914f47f3a058d20fdbebeb83
Source dataset
uspto-grants-2014_06
Patent number
US08748452B2

Reaction notes

Loading…