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Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines
Author(s) -
Fritz Sven P.,
Mumtaz Amara,
Yar Muhammad,
McGarrigle Eoghan M.,
Aggarwal Varinder K.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100337
Subject(s) - chemistry , morpholine , amine gas treating , trifluoromethanesulfonate , reboxetine , hydrochloride , organic chemistry , hydrolysis , protecting group , combinatorial chemistry , catalysis , biochemistry , alkyl , receptor , reuptake inhibitor , serotonin
1,2‐Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N ‐sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyldiphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug ( S , S )‐reboxetine.