ChemicalBook CAS DataBase List 1-Aminoethylphosphonic acid diethyl

1-Aminoethylphosphonic acid diethyl synthesis

12synthesis methods

Product Name:1-Aminoethylphosphonic acid diethyl
CAS Number:54788-35-1
Molecular formula:C6H16NO3P
Molecular Weight:181.17

Phosphonic acid, [1-[(trifluoroacetyl)amino]ethyl]-, diethyl ester (9CI)

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54788-35-1
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Yield:54788-35-1 97%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 20; for 5 h;Reflux;

Steps:

Diethyl 1-aminoethylphosphonate or D/L-Fos diethyl ester (9)

Diethyl (1-(2,2,2-trifluoroacetamido)ethyl)phosphonate (8) (20.0 mmol, 5.6 g) was dissolved in ethanol (200 ml) andexcess sodium borohydride (200.0 mmol, 7.7 g) was added slowly with stirring. The resulting mixturewas stirred at room temperature for 1 hour, then heated at reflux for 4 hours. The mixture was cooledto room temperature and the solvent was removed in vacuo to afford a white solid, which wasdissolved in saturated NaHCO3 (96 g/L) (60 mL) with the addition of 10% aqueous K2CO3 (20 mL).The product was extracted into DCM (6 x 30 mL) and dried over MgSO4. The filtrate was concentratedin vacuo to afford a pale yellow liquid and purified by column chromatography using a gradientelution (DCM (100) to DCM/MeOH (90:10)) to afford 9 as a yellow liquid, a mixture of enantiomers(3.5 g, 19.3 mmol, 97%); max/cm-1 3431 (NH), 1215 (P = O), 1020 (P-O-C), 967 (P-O-C); 1H NMR (300MHz, CDCl3) δH 1.26 (6H, t, 3JH-H = 7.2 Hz, 2 x OCH2CH3), 1.34 (3H, dd, 3JH-P = 17.7 Hz, 3JH-H = 7.2 Hz,CH3-2), 1.68 (2H, br, NH2), 3.02-3.12 (1H, m, CH-1), 4.06-4.17 (4H, m, 2 x OCH2CH3); 13C NMR (75MHz, CDCl3) δC 16.4 (OCH2CH3), 16.5 (OCH2CH3), 17.2 (CH3-2), 44.2 (d, 1JC-P = 148.5 Hz, CH-1), 62.1(d, 2JC-P = 7.5 Hz, OCH2CH3), 62.1 (d, 2JC-P = 7.5 Hz, OCH2CH3); 31P-1Hdecoup NMR (121 MHz, CDCl3) δP29.6; HRMS (NSI) calcd for (C6H17NO3P)+, MH+: 204.0760, found 204.0762. LCMS purity >95% (C-18reversed phase, MeOH-H2O).

References:

Anderson, Rosaleen J.;Gray, Mark;Marrs, Emma C. L.;Ng, Keng Tiong;Orenga, Sylvain;Perry, John D. [Molecules,2020,vol. 25,# 7] Location in patent:supporting information

Carbamic acid, N-[1-(diethoxyphosphinyl)ethyl]-, phenylmethyl ester

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References

Diethyl N-hydroxyethanimidoylphosphonate

53145-08-7
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References

Phosphonic acid, (1-nitroethyl)-, diethyl ester

60593-26-2
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References

75-07-0 Synthesis

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References