Methanol → methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

HRID 19736Notes

Reaction equation

HRID 19736 reaction equation
Cl.[N:2]1[C:10]2[CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:14]O>S(=O)(=O)(O)O>[CH3:14][O:12][C:11]([CH:8]1[CH2:9][C:10]2[N:2]=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:7]1)=[O:13]

Participants

4

Reactant 2

HCID 887MethanolHCID 685628996,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid hydrochloride

Product 1

HCID 14639626methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution 6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid hydrochloride (Example 88; 0.640 g, 3.21 mmol) and concentrated sulphuric acid (3 drops) in methanol (100 ml) is heated to reflux for 3 hours. The solvent is evaporated, the residue is treated with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic phases are washed with brine, dried (MgSO4) and evaporated to afford 6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid methyl ester, MH+178.

Workup

  1. temperatureto reflux for 3 hours
  2. customThe solvent is evaporated
  3. additionthe residue is treated with saturated aqueous NaHCO3
  4. extractionextracted with EtOAc
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-2c0cd0bc50d447c498c33c72bc4f4d4d
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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