Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1989-08-21
1990-11-27
Hollrah, Glennon H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
544175, 544358, 544387, 546190, 548571, 564344, 568310, 568312, 568315, 568316, 568317, 568318, C07C22100, C07C22300, C07C22500
Patent
active
049737562
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.
REFERENCES:
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Barf Gerrit A.
Borcherding David R.
Hoeve Wolter T.
Koek Johannes N.
Wynberg Hans
Hollrah Glennon H.
Marion Laboratories, Inc.
Rand Scott C.
Rudy Christopher J.
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