Chlorination/cyclodehydration of amino alcohols with SOCl2: an old reaction revisited.
A simple, one-pot preparation of cyclic amines via efficient chlorination of amino alcohols with use of SOCl(2) has been developed. This approach obviates the need for the classical N-protection/O-activation/cyclization/deprotection sequence commonly employed for this type of transformation. The reaction pathways and the general scope of this method have also been investigated.
Xu
Feng
F
Department of Process Research, Merck Research Laboratory, Rahway, New Jersey 07065, USA. feng_xu@merck.com
Simmons
Bryon
B
Reamer
Robert A
RA
Corley
Edward
E
Murry
Jerry
J
Tschaen
David
D
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003681:Dehydration; D054879:Halogenation; D015394:Molecular Structure; D013237:Stereoisomerism; D013461:Sulfur Oxides / Q000737:chemistry*
D000605:Amino Alcohols; D013461:Sulfur Oxides; C023589:thionyl chloride