Synthesis of (4-fluoro-3-piperidin-4-yl-benzyl)-carbamic acid tert-butyl ester and intermediates thereof
US8633321B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Mar 22, 2012 |
| Grant date | Jan 21, 2014 |
| Priority date | — |
| Expiry date | Mar 22, 2032 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F5/025
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention is an improved method for the preparation of (4-fluoro-3-pyridin-4-yl-benzyl)-carbamic acid tert-butyl ester, compound of formula I. The invention is directed to a method of synthesis for the compound of formula I in three steps, comprising formation of 5-((tert-butoxycarbonyl)aminomethyl)-2-fluorobenzeneboronic acid (compound 11), reaction of compound 11 under Suzuki coupling conditions to yield (4-fluoro-2-pyridin-4-yl-benzyl)-carbamic acid tert-butyl ester and selective hydrogenation of the aforementioned product under hydrogenation conditions yields compound I. The invention is also directed to the intermediates 5-((tert-butoxycarbonyl)amino-methyl)-2-fluorobenzeneboronic acid (compound 11), and (4-fluoro-3-pyridin-4-yl-benzyl)-carbamic acid tert-butyl ester (compound 13).
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.