Multigram Preparation of BRD4780 Enantiomers and Assignment of Absolute Stereochemistry.
J Org Chem
| Authors | |
| 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. |
| Year of Publication | 2021
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| Journal | J Org Chem
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| Volume | 86
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| Issue | 5
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| Pages | 4281-4289
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| Date Published | 2021 Mar 05
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| ISSN | 1520-6904
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| DOI | 10.1021/acs.joc.0c02520
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| PubMed ID | 33618515
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