Formaldehyde → HCID 14541445, compound

HRID 345326Notes

Reaction equation

HRID 345326 reaction equation
[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].[CH2:19]=O>[Pd].CO>[CH3:19][N:13]1[CH2:14][CH2:15][C@H:10]([CH2:9][P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][C@@H:12]1[C:16]([NH2:18])=[O:17]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 14541441HCID 14541441, compound

Product 1

HCID 14541445HCID 14541445, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 500 mg of cis-4-diethylphosphonomethyl-2-piperidinecarboxamide, 3 ml of 37% aqueous formaldehyde, 50 ml of methanol and 500 mg of 10% palladium on carbon catalyst is hydrogenated at 3 atmospheres pressure for 16 hours. The solvent is removed and the residue chromatographed on silica gel with 10% methanol/methylene chloride as the eluant to afford cis-1-methyl-4-diethylphosphonomethyl-2-piperidinecarboxamide. This product is refluxed for 16 hours in 6N hydrochloric acid followed by treatment with propylene oxide to yield cis 1-methyl-4-phosphonomethyl-2-piperidinecarboxylic acid, m.p. 256°-260°.

Workup

  1. customThe solvent is removed
  2. customthe residue chromatographed on silica gel with 10% methanol/methylene chloride as the eluant

Sources & evidence

ORD record
ord-0191811dc5e24b11bd11cd48f2a10953
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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