Parallel protocol for the selective methylation and alkylation of primary amines.
One of the still unresolved problems in parallel synthesis is the availability of a general and rapid method for the transformation of a primary amine into the corresponding secondary amine without the issue of polyalkylation. Following the Fukuyama method, which is based on the alkylation of o-nitrobenzenesulfonamides, followed by removal of the sulfonyl group, we have developed a simple protocol which can be easily applied to parallel synthesis making use of supported reagents and scavengers. To verify the robustness of the method, a small representative array of secondary amines have been prepared. Moreover, taking advantage of the possibility to use different supported reagents in the same pot, we also prepared, starting from primary amines, a series of differently substituted tertiary amines.
Cardullo
Francesca
F
GlaxoSmithKline, Medicines Research Centre, Via A. Fleming 4, 37135 Verona, Italy.
Donati
Daniele
D
Fusillo
Vincenzo
V
Merlo
Giancarlo
G
Paio
Alfredo
A
Salaris
Margherita
M
Solinas
Antonio
A
Taddei
Maurizio
M
D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines