4-(Diethylphosphonomethyl)-2-pyridinecarboxamide → trans 4-(Diethylphosphonomethyl)-2-piperidinecarboxamide
Reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH2:18])=[O:17])[CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>C(O)(=O)C.[Pt]=O>[CH2:1]([O:3][P:4]([CH2:9][C@@H:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([C:16]([NH2:18])=[O:17])[CH2:11]1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1.19 g of 4-(diethylphosphonomethyl)-2pyridinecarboxamide and 0.75 g of platinum oxide in 30 ml of acetic acid is hydrogenated at 3 atmospheric pressure for 6 hours at room temperature. The reaction mixture is filtered and the solvent is removed in vacuo. The residue is dissolved in methylene chloride and washed with a small volume of saturated sodium bicarbonate solution. After drying over magnesium sulfate, a methylene chloride solution of a 2:1 mixture of cis and trans 4-(diethylphosphonomethyl)-2-piperidinecarboxamide is obtained. After 3 days at room temperature this mixture isomerizes to the more stable cis isomer. Removal of the solvent in vacuo affords cis-4-(diethylphosphonomethyl)-2-piperidinecarboxamide as an oil, which is converted to the hydrochloride salt, melting at 155°-158°.
Workup
- filtrationThe reaction mixture is filtered
- customthe solvent is removed in vacuo
- dissolutionThe residue is dissolved in methylene chloride
- washwashed with a small volume of saturated sodium bicarbonate solution
- dry with materialAfter drying over magnesium sulfate
- additiona methylene chloride solution of a 2:1 mixture of cis
Sources & evidence
- ORD record
- ord-fb27be3a041f470c809ebd731cd3a20c
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05057506
Reaction notes
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