The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Nov. 27, 1990
Filed:
Aug. 21, 1989
Hans Wynberg, Groningen, NL;
Wolter T Hoeve, Eelde, NL;
Gerrit A Barf, Groningen, NL;
Johannes N Koek, Sauwerd, NL;
David R Borcherding, Roeland Park, KS (US);
Marion Laboratories, Inc., Kansas City, MO (US);
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.