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.
Department of Process Research, Merck Research Laboratory, Rahway, New Jersey 07065, USA. feng_xu@merck.com
Feng
F
Xu
Bryon
B
Simmons
Robert A
RA
Reamer
Edward
E
Corley
Jerry
J
Murry
David
D
Tschaen
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