Synthesis of cyclohexane derivatives useful as sensates in consumer products
US8754259B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Mar 20, 2013 |
| Grant date | Jun 17, 2014 |
| Priority date | — |
| Expiry date | Mar 20, 2033 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2601/14
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.