Organocatalytic process for asymmetric synthesis of decanolides
US-2016272608-A1 · Sep 22, 2016 · US
Organocatalytic process for asymmetric synthesis of decanolides
US9809566B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9809566-B2 |
| Application number | US-201615167337-A |
| Country | US |
| Kind code | B2 |
| Filing date | May 27, 2016 |
| Priority date | Sep 6, 2012 |
| Publication date | Nov 7, 2017 |
| Grant date | Nov 7, 2017 |
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Abstract
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The present invention discloses organocatalytic process for asymmetric synthesis of highly enantioselective decanolide compounds in high yield with >99% ee. Further, the present invention disclose cost effective, improved organocatalytic process for asymmetric synthesis of highly enantioselective decanolides compounds from non-chiral, cheap, easily available raw materials.
First claim
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We claim: 1. An organo catalytic process for the preparation of decanolides of Formula Ic wherein the said process comprising the steps of: i) allylboration of aldehyde (1) in presence of allyldiisopinocamphenylborane at temperature in the range of −120° C. to −80° C. for 1-2 hours in non-polar organic solvents selected from the group consisting of diethyl ether, pentane, cyclopentane, benzene, toluene, 1,4-dioxane, chloroform, and mixtures thereof followed by treatment with NaOH and aqueous H 2 O 2 to obtain chiral allylic alcohol (3) ii) esterification of allylic alcohol (3) with butyldimethylsilyl(TBS) protected carboxylic acid (15) in presence of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine in DCM at temperature range 0° to 30° C. for 5 to 8 hours with subsequent deprotection of TBS in presence of tetra-n-butylammonium fluoride in THF for 6-8 hours yields allylic alcohol (17) and iii) ring closing metathesis reaction of compound (17) in presence of Grubbs II catalyst (5 to 15%) in dry CH 2 Cl 2 for 18-24 hours to obtain decanolides of Formula Ic.
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Optical isomers · CPC title
- C07D313/00Primary
Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom · CPC title
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- What does patent US9809566B2 cover?
- The present invention discloses organocatalytic process for asymmetric synthesis of highly enantioselective decanolide compounds in high yield with >99% ee. Further, the present invention disclose cost effective, improved organocatalytic process for asymmetric synthesis of highly enantioselective decanolides compounds from non-chiral, cheap, easily available raw materials.
- Who is the assignee on this patent?
- Council Scient Ind Res
- What technology area does this patent fall under?
- Primary CPC classification C07D313/00. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Nov 07 2017 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 3 related publications on this page (citations in our corpus or others sharing the same primary CPC).