55686-29-8Relevant articles and documents
Efficient synthesis of the azabicyclo[3.3.1]nonane ring system in the alkaloid methyllycaconitine using bis(alkoxymethyl)alkylamines as aminoalkylating agents in a double Mannich reaction
Brimble, Margaret A.,Brocke, Constanze
, p. 2385 - 2396 (2005)
The double Mannich reaction of cyclic β-keto esters with bis-(alkoxymethyl)alkylamines provides an efficient and versatile method for the construction of azabicyclo[3.3.1]nonanes and azabicyclo[3.2.1]octanes. The optimum conditions for efficient reaction involve use of the activator trichloromethylsilane in acetonitrile as solvent at ambient temperature. The utility of this synthetic method is further demonstrated by the facile synthesis of several AE ring analogues 39, 42 of the alkaloid methyllycaconitine by appendage of the key N-(methylsuccininimido)anthranilate pharmacophore to the N-(3-phenylpropyl)-substituted double Mannich adducts 18, 27. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
The use of bis(aminol) ethers derived from aliphatic primary amines in the synthesis of secondary and tertiary amines
Heaney, Harry,Papageorgiou, George
, p. 3473 - 3486 (2007/10/03)
A series of bis(aminol) ethers were prepared from primary aliphatic amines and benzylamine together with formaldehyde and either ethanol or methanol; they were reacted with electrophiles to give N-alkyl-N-alkoxymethyl-methyleneiminium salts which gave mixtures of secondary and tertiary amines in reactions with electron rich aromatic compounds: sequential reactions with two different nucleophiles gave the expected tertiary amines.
