26735-10-4Relevant articles and documents
A one-pot selective synthesis of N-Boc protected secondary amines: Tandem direct reductive amination/N-Boc protection
Neelarapu, Raghupathi,Petukhov, Pavel A.
, p. 7056 - 7062 (2012/08/28)
A one-pot tandem direct reductive amination of aldehydes with primary amines resulting in N-Boc secondary amines using a (Boc)2O/sodium triacetoxyborohydride (STAB) system is reported. The tandem procedure is efficient, selective, and versatile, giving excellent yields of N-Boc protected secondary amines even in those cases where the products are prone to intramolecular lactamization.
Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives
Decker, Michael,Nguyen, Thi Thanh Huyen,Lehmann, Jochen
, p. 4567 - 4578 (2007/10/03)
The mechanism of lactamization of corresponding lactones was investigated by means of gas chromatography and synthesis of possible intermediates as references. Lactones react with amines via the amino acid with subsequent elimination of water to the corresponding lactams. In the first step, also hydroxyamides are in equilibrium with the lactones and amines, respectively, which are not able to form the amide though. This mechanism opens a new approach for the synthesis of Nβ-disubstituted tryptamines.
