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The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 10450282 B1

PDFFull Text
Date of Patent:
Oct. 22, 2019

Filed:

Aug. 05, 2016

Stereospecific process for 3-heterocyclylcycloaliphatic-1,2-diols

Applicant:

Icahn School of Medicine AT Mount Sinai, New York, NY (US);

Inventors:

Michael Ohlmeyer, Plainsboro, NJ (US);

Nilesh Zaware, Briarwood, NY (US);

David Kastrinsky, Fair Lawn, NJ (US);

Assignee:

ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI, New York, NY (US);

Attorneys:

Heslin Rothenberg Farley & Mesiti, P.C.

Philip Hansen

Primary Examiner:

Susanna Moore

Int. Cl.
CPC ...
C07D 498/04 (2006.01); C07D 209/86 (2006.01); C07D 209/88 (2006.01); C07D 275/06 (2006.01); C07D 291/08 (2006.01); C07D 265/38 (2006.01); C07D 401/04 (2006.01); C07D 405/04 (2006.01); C07D 413/04 (2006.01); C07D 417/04 (2006.01); C07D 307/30 (2006.01); C07D 285/01 (2006.01); C07D 301/14 (2006.01); C07D 309/28 (2006.01); C07D 419/04 (2006.01);
U.S. Cl.
CPC ...
C07D 265/38 (2013.01); C07D 209/86 (2013.01); C07D 275/06 (2013.01); C07D 285/01 (2013.01); C07D 291/08 (2013.01); C07D 301/14 (2013.01); C07D 307/30 (2013.01); C07D 309/28 (2013.01); C07D 401/04 (2013.01); C07D 405/04 (2013.01); C07D 413/04 (2013.01); C07D 417/04 (2013.01); C07D 419/04 (2013.01); C07D 498/04 (2013.01); C07B 2200/07 (2013.01); Y02P 20/582 (2015.11);
Abstract

A process for the stereoselective synthesis of chiral 3-heterocyclyl-1,2-dihydroxy cyclohexanes is disclosed. The process involves reacting a tricyclic nitrogenous heterocycle with an allyl carbonate in the presence of a chiral palladium catalyst followed by oxidation of the olefinic bond to provide 3-heterocyclyl-1,2-dihydroxy cyclohexanes, cyclopentanes and corresponding alicyclic heterocycles. Also disclosed are methods for converting the heterocyclyl-1,2-dihydroxy cyclohexanes to 2-amino-6-(heteroaryl)cyclohexanols (and related cyclic compounds).

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