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

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 racemizat...

Full description

Saved in:
Bibliographic Details
Published in:Organic process research & development 2016-10, Vol.20 (10), p.1717-1720
Main Authors: Karmakar, Sukhen, Byri, Vijay, Gavai, Ashvinikumar V, Rampulla, Richard, Mathur, Arvind, Gupta, Anuradha
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.6b00207