cas 16414-63-4, 1-aminopropan-2-one 4-methylbenzenesulfonate (1:1)

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An optimized version of Gabriel-type nucleophilic amination
N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t- butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-I. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol-affords ammonium tosylates 3a-I in reasonable yields.
Zwierzak, Andrzej
p. 2287 - 2293
(2007/10/03)

Reaction of azides with trimethyl phosphite in the presence of water: a chemoselective synthesis of functionalized phosphoramidates
The reductive phosphorylation of azides with trimethyl phosphite and water in THF leads to the corresponding phosphoramidates which are protected primary amines in excellent yields.The P-N bond in these derivatives may be easily cleft in acidic medium to give the primary amine salts.Some examples are reported.The bis-anion 4 obtained by metallation of 3b is C-alkylated at low temperature leading to new phosphoramidates. 3i and 3j derived from α-azidoketones could not be transformed into the corresponding α-aminoketone salts.The use of methyl diphenylphosphinite in place of trimethyl phosphite leads to the diphenylphosphinamide 7 which, when treated with para-toluenesulfonic acid monohydrate in ether, gives the corresponding α-aminoacetone salt 8 in good yield.Keywords: azides / reductive phosphorylation / phosphoramidates / chemoselective reduction / functionalized primary amines
Zidani, A.,Carrie, R.,Vaultier, M.
p. 71 - 75
(2007/10/02)