Cyclopentanone → 5H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)

HRID 518580Notes

Reaction equation

HRID 518580 reaction equation
N1[CH:6]=[CH:5][N:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])N=1.[C:12]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCC1>C1(C)C=CC=CC=1>[C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:13]2[CH2:14][CH2:15][CH2:16][C:12]=2[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 31268PyrrolidineHCID 12559180Ethyl 1,2,4-triazine-3-carboxylate

Product 1

HCID 450986655H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)Yield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 1,2,4-triazine-3-carboxylate (7 g, 45.8 mmol), cyclopentanone (4.9 mL, 55.0 mmol), and pyrrolidine (4.6 mL, 55.0 mmol) in toluene (100 mL) were heated to reflux for 12 h. The mixture was purified by column on silica gel chromatography (PE/EtOAc=5:1) to give the title compound (2.02 g, 25%) as a brown oil. LCMS: 192 (M+1)+

Workup

  1. temperatureto reflux for 12 h
  2. customThe mixture was purified by column on silica gel chromatography (PE/EtOAc=5:1)

Sources & evidence

ORD record
ord-86a978aa0997469198df29d32ff2fb9f
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

Loading…