Hydroxylated ene ketones, acetylenic grignards and hydroxylated yne ketones therefrom
US4973756A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Aug 21, 1989 |
| Grant date | Nov 27, 1990 |
| Priority date | — |
| Expiry date | Aug 21, 2009 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2601/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
An alpha-hydroxyl-alpha,alpha-di(inert-substituted)-gamma',delta'-yne ketone can be prepared by a procedure comprising contacting an acetylenic Grignard reagent with an alpha-hydroxyl-alpha,alpha-di(inert substituted)-alpha',beta'-ene ketone, and the alpha-hydroxyl-alpha,alpha-di(inert-substituted)-alpha',beta'-ene ketone can be prepared by a procedure comprising steps of contacting, first, an alkoxy allene with a lithium donating organic agent, second, product of the first step with a di(inert-substituted)ketone, and third, product of the second step with an acidic substance. For example, 1-cyclobutyl-7-(N,N-dimethylamino)-1-hydroxy-1-phenylhept-5-yn-2-one, hydrochloride salt (ML-1012), can be prepared by the reaction of 1-cyclobutyl-1-hydroxy-1-phenylbut-3-en-2-one and 1-(N,N-dimethylamino)-2-propyn-3-magnesium chloride, followed by salt formation with hydrogen chloride gas, and the 1-cyclobutyl-1-hydroxy-1-phenylbut-3-en-2-one can be prepared by the serial reactions of (1) 1-methoxy allene with n-butyllithium, (2) product of this first step with cyclobutylphenyl ketone, and (3) product of this second step with sulfuric acid.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.