DiethylN-Benzylideneaminomethylphosphonate

Abstract

[50917-73-2] C12H18NO3P (MW 255.25) InChI = 1S/C12H18NO3P/c1-3-15-17(14,16-4-2)11-13-10-12-8-6-5-7-9-12/h5-10H,3-4,11H2,1-2H3 InChIKey = REXOGTNRQYAOQG-UHFFFAOYSA-N (reagent for preparation of β-lactams1 and α-aminophosphonic acids;3 agent for quaternary carbon formation4) Physical Data: bp 145–149 °C/0.05 mmHg. Solubility: sol most organic solvents. Form Supplied in: light yellow oil. Analysis of Reagent Purity: readily ascertained by NMR. Preparative Methods: 1,3,5-tribenzylhexahydro-sec-triazine is reacted with Diethyl Phosphonite at 100 °C to yield N-benzylaminomethylphosphonate. N-Debenzylation with H2–Palladium on Carbon and subsequent Schiff base formation with PhCHO affords the title reagent in virtually quantitative yield.1a Alternatively, the reagent may be prepared from the N,N-bis(TMS)aminomethylphosphonate and PhCHO in the presence of a catalytic amount of Trimethylsilyl Trifluoromethanesulfonate.2 A different approach to the aminomethylphosphonate intermediate starts with conversion of N-hydroxymethylphthalimide to the N-bromomethyl compound followed by an Arbuzov reaction with Triethyl Phosphite. Treatment of the resultant phthalimidomethylphosphonate with Hydrazine yields diethyl aminomethylphosphonate which is then subjected to imine formation with PhCHO.4a Purification: distillation at reduced pressure. Handling, Storage, and Precautions: stable to air and moisture. Conveniently stored under N2 at ambient temperature or lower. Shelf life undetermined.