Kinetic resolution of racemic hydroxy ester via asymmetric catalytic hydrogenation and application thereof
US10676422B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Aug 8, 2015 |
| Grant date | Jun 9, 2020 |
| Priority date | — |
| Expiry date | Mar 10, 2036 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D309/30
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention relates to kinetic resolution of racemic δ-hydroxyl ester via asymmetric catalytic hydrogenation and an application thereof. In the presence of chiral spiro pyridyl phosphine ligand Iridium catalyst and base, racemic δ-hydroxyl esters were subjected to asymmetric catalytic hydrogenation to obtain extent optical purity chiral δ-hydroxyl esters and corresponding 1,5-diols. An optically active chiral δ-hydroxyl ester and 1,5-diols can be obtained at very high enantioselectivity and yield with relatively low usage of catalyst. The chiral δ-hydroxyl ester and 1,5-diols obtained by using the method can be used as a critical raw material for asymmetric synthesis of chiral drugs (R)-lisofylline and natural drugs (+)-civet, (−)-indolizidine 167B and (−)-coniine.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.