Diethyl (benzylamino)methylphosphonate → Diethyl (aminomethyl)phosphonate

HRID 1594535Notes

Reaction equation

HRID 1594535 reaction equation
C([NH:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 10923173Diethyl (benzylamino)methylphosphonate

Product 1

HCID 1596920Diethyl (aminomethyl)phosphonateYield 37,113.398%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of diethyl (N-benzyl)aminomethylphosphonate (2.5 g, 9.7 mmol) in 30 ml of EtOH and 0.5 g of Pd(OH)2 was stirred under an atmosphere of hydrogen (1 atm) overnight. The reaction was filtered through celite and concentrated to give diethyl aminomethylphosphonate (600 mg, 3.6 mol). The crude phosphonate was dissolved in 30 ml of dichloromethane, cooled to 0° C., and treated with 4-phenoxybenzenesulfonyl chloride (800 mg, 3 mol) and triethylamine (1 ml, 7.2 mol). The ice bath was removed, the reaction was stirred for 4 h, and 20 mL of 5% HCl was added. The aqueous layer was extracted with 30 mL of dichloromethane, and the combined dichloromethane fractions were washed with brine, dried over magnesium sulfate, and concentrated to give diethyl[(4-phenoxy)benzenesulfonyl]aminomethylphosphonate (1.26 g, 88%) as a clear oil.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-86908a051cbc4d55ad8c1e7f3de8412d
Source dataset
uspto-grants-2001_09
Patent number
USH0001992H1

Reaction notes

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