A Fit-for-Purpose Synthesis of (R)‑2-Methylazepane

The preparation of new RSV inhibitors required an efficient synthesis of (R)-2-methylazepane ((R)-1) amenable to large-scale production to support preclinical studies. After consideration of different options, an efficient five-step synthesis relying on the preparation of the racemic N-Boc precursor...

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Bibliographic Details
Published inOrganic process research & development Vol. 24; no. 5; pp. 729 - 733
Main Authors Guizzetti, Sylvain, Michaut, Antoine, Federspiel, Guillaume, Eymard, Julien, Caron, Isabelle, Quatrevaux, Sabrina, Daras, Etienne, Jolly, Sandrine, Guillemont, Jérôme, Lançois, David
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.05.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
(R)-2-methylazepane
chiral SFC
RSV inhibitors
route scouting
REAGENTS
REDUCTION
SEQUENCE
BECKMANN REARRANGEMENT
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Summary:The preparation of new RSV inhibitors required an efficient synthesis of (R)-2-methylazepane ((R)-1) amenable to large-scale production to support preclinical studies. After consideration of different options, an efficient five-step synthesis relying on the preparation of the racemic N-Boc precursor and its purification by chiral SFC was developed and successfully implemented on a 400 g scale.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00425