You are here

J Org Chem DOI:10.1021/acs.joc.0c02520

Multigram Preparation of BRD4780 Enantiomers and Assignment of Absolute Stereochemistry.

Publication TypeJournal Article
Year of Publication2021
AuthorsChamberlain, BT, Vincent, M, Nafie, J, Müller, P, Greka, A, Wagner, FF
JournalJ Org Chem
Volume86
Issue5
Pages4281-4289
Date Published2021 Mar 05
ISSN1520-6904
Abstract

The development of a multigram synthesis of 3--isopropylbicyclo[2.2.1]heptan-2--amine hydrochloride () (also known as BRD4780 and AGN-192403) is described. The process involves protection of the amine as 4-nitrobenzyl carbamate, pNZ, which enables chiral SFC chromatography. The absolute configuration (AC) of the individual enantiomers has been determined by Mosher's amide method, VCD spectroscopy, and X-ray crystallography. We highlight the VCD approach as a rapid and effective means of AC determination that can be deployed directly on the target compounds.

DOI10.1021/acs.joc.0c02520
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/33618515?dopt=Abstract

Alternate JournalJ Org Chem
PubMed ID33618515