Organic Process Research and Development, volume 20, issue 10, pages 1717-1720
Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors
Sukhen Karmakar
1
,
Vijay Byri
1
,
Ashvinikumar V Gavai
2
,
Richard Rampulla
2
,
Arvind Mathur
2
,
Anuradha Gupta
1
1
Department
of Discovery Synthesis, Biocon Bristol-Myers Squibb Research Centre, Biocon Park, Bommasandra IV Phase, Jigani Link Road, Bengaluru 560099, India
|
2
Bristol-Myers Squibb Company, P.O Box 4000, Princeton, New Jersey 08543-4000, United States
|
Publication type: Journal Article
Publication date: 2016-10-05
scimago Q1
wos Q1
SJR: 0.900
CiteScore: 6.9
Impact factor: 3.1
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An enantioselective synthesis of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one (S-1) is described. The key step in the sequence involved crystallization-induced dynamic resolution (CIDR) of compound 7 using Boc-d-phenylalanine as a chiral resolving agent and 3,5-dichlorosalicylaldehyde as a racemization catalyst to afford S-1 in 81% overall yield with 98.5% enantiomeric excess.
Found
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