Methanol → methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureto reflux for 3 hours
- customThe solvent is evaporated
- additionthe residue is treated with saturated aqueous NaHCO3
- extractionextracted with EtOAc
- washThe combined organic phases are washed with brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-2c0cd0bc50d447c498c33c72bc4f4d4d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745462B2
Reaction notes
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