3- Aminopropyl phosphinic acid

Several communications, summarized in Scheme 14, have described the synthesis of many amino-substituted dialkylphosphinic acids and phosphonic acids, and also many similarly substituted hydrogenphosphinic acids. Alkylation of the phosphinates (272) (R = H or Me, = Et, R = H) yields the corresponding (273) which, in a single step, are convertible into the useful intermediates (274). With 1,2-unsaturated nitriles, for example, the (3-aminopropyl)phosphinic acids... 

The application of 3-aminopropyl phosphine (3) [41,46] as a building block for incorporation into -COOH functionalized frameworks provides an excellent example of the utility of preformed primary phosphine frameworks (Scheme 8) [46]. The reactions involved Michael addition of ferf-butyl acrylate to malonic acid dimethyl ester to produce the intermediate adduct, 2-methoxycarbonyl-pentanedioc acid 5-ferf-butyl ester 1-methyl ester, which upon treatment with trifluro-acetic acid (TFA) produced the corresponding diester acid,2-methoxy-carbonyl-pentanedioic acid 1-methyl ester, in near quantitative yield. It is remarkable to note that the reaction of NH2(CH2)3PH2 (3) with the diester acid is highly selective as the -COOH group remained unattacked whereas the reaction occurred smoothly and selectively at the -COOMe groups to pro-... 

OHDPAT, 8-hydroxy-2(di- -propylamino)tetralin ACPD, trans-1 -amino-cyclopenty 1 -1,3 -dicarboxylate AMP A, DL-cr-amino-3-hydroxy-5-methylisoxazole-4-propionate BIMU8, [endo-A-8-methyl-8-azabicyclo(3.2.1)oct-3-yl]-2,3-dihydro-3-isopropyl-2-oxo-177-benzimidazol-l-carboxamide hydrochloride CGP 35348, 3-aminopropyl(diethoxymethyl)phosphinic acid CNQX, 6-cyano-7-nitroquinoxaline-2,3-dione CP 99994, (+)-(2 , 3A)-3-(2-methoxybenzylamino)-2- ... 

Aminopropyl(cyclohexylmethyl)phosphinic acid (46, R = CH2C6H11, R , R, R = H) has been patented as an antiepileptic. When given to epileptic rats (400 mg kg i.p.) it eliminated spike and wave discharges after 20 min. ... 

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