Methods of synthesis of (1R,2R,5R)-5-amino-2-methyl-cyclohexanol hydrochloride and intermediates useful therein

US11780801B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-11780801-B2
Application numberUS-202117518552-A
CountryUS
Kind codeB2
Filing dateNov 3, 2021
Priority dateJul 24, 2015
Publication dateOct 10, 2023
Grant dateOct 10, 2023

How to read this patent

A practical reading order for non-experts. Skip the full description unless you need deep technical detail.

  1. Title

    What the patent document calls the invention.

  2. Abstract

    A short plain-language summary of the technical disclosure.

  3. Assignees and inventors

    Who owns or filed the patent and who is credited as inventor.

  4. Key dates

    Filing, priority, publication, and grant dates set the timeline.

  5. First independent claim

    The legal scope of protection — read this for what is actually claimed.

  6. CPC / IPC classifications

    Technology tags used to group this patent with similar filings.

  7. Citations and related patents

    Prior art links and similar publications in this corpus.

Abstract

Official abstract text for this publication.

Provided herein are methods and intermediates for making (1R, 2R, 5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.

First claim

Opening claim text (preview).

What is claimed is: 1. A method for preparing a compound of formula (9): the method comprising contacting a compound of formula (8): with a mixture of a reducing agent, a chiral auxiliary and a Lewis acid in a solvent, followed by treatment with an oxidant in the presence of a base. 2. The method of claim 1 , wherein the reducing agent is NaBH 4 . 3. The method of claim 1 , wherein the chiral auxiliary is α-pinene. 4. The method of claim 1 , wherein the Lewis acid is BF 3 ·Et 2 O. 5. The method of claim 1 , wherein the solvent is THF or EtOH. 6. The method of claim 1 , wherein the solvent is THF. 7. The method of claim 1 , wherein the solvent is EtOH. 8. The method of claim 1 , wherein the oxidant is H 2 O 2 or oxone. 9. The method of claim 1 , wherein the oxidant is H 2 O 2 . 10. The method of claim 1 , wherein the base is NaOH. 11. The method of claim 1 , wherein the reducing agent is NaBH 4 , the chiral auxiliary is α-pinene, the Lewis acid is BF 3 ·Et 2 O, and the solvent is THF. 12. The method of claim 11 , wherein the oxidant is H 2 O 2 and the base is NaOH.

Assignees

Inventors

Classifications

  • C07C213/02Primary

    by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

  • from carboxylic acid esters or lactones · CPC title

  • by addition to unsaturated carbon-to-carbon bonds · CPC title

  • from or via amides · CPC title

  • Separation of optical isomers · CPC title

Patent family

Related publications grouped by family.

External sources

Frequently asked questions

Answers are generated from the same data shown on this page.

What does patent US11780801B2 cover?
Provided herein are methods and intermediates for making (1R, 2R, 5R)-5-amino-2-methylcyclohexanol hydrochloride, which are useful for the preparation of compounds useful for the treatment of a disease, disorder, or condition associated with the JNK pathway.
Who is the assignee on this patent?
Celgene Corp
What technology area does this patent fall under?
Primary CPC classification C07C213/02. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Oct 10 2023 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 12 related publications on this page (citations in our corpus or others sharing the same primary CPC).