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US 5,665,882 AGranted
Pyridyl ethylation of lactams
AssigneeMerck & Co., Inc.
InventorsJohn Y. L. Chung, Dalian Zhao, James M. McNamara, David L. Hughes
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Abstract
The invention is a highly efficient synthesis for making compounds of formula: ##STR1## wherein n=0, 1, R is C.sub.1-4 alkyl or benzyl; and R.sup.1, when present, is C.sub.1-4 alkyl, OH, O--C.sub.1-4 alkyl or S--C.sub.1-4 alkyl. The process involves silane-mediated conjugation of 4-vinylpyridine to a substituted lactam.
Claims10
A process for preparing compounds of the following formula:
- ##STR49## wherein R is C.sub.1-4 alkyl or benzyl;
- and
- R.sup.1, when present, is C.sub.1-4 alkyl, OH, O--C.sub.1-4 alkyl, or S--C.sub.1-4 alkyl;
- comprising
- a) alkylating a lactam having the formula ##STR50## to form ##STR51## b) dissolving the substituted lactam ##STR52## in a non-aqueous solvent solution, c) dissolving a silyl derivative in the solution of b), and
- d) adding 4-vinylpyridine to the solution of c) to form ##STR53##
3 more elements
A compound having the structure ##STR54## wherein R is C.sub.1-4 alkyl or benzyl;
- and
- R.sup.1, when present, is C.sub.1-4 alkyl, OH, O--C.sub.1-4 alkyl, or S--C.sub.1-4 alkyl.
A compound which is ##STR55##
A process for preparing a compound of the invention which comprises
- a) dissolving a lactam having the structure ##STR57## wherein R.sup.1, when present, is C.sub.1-4 alkyl, OH, O--C.sub.1-4 alkyl, or S--C.sub.1-4 alkyl,
- in a non-aqueous solvent system comprising a non-aqueous solvent, a tertiary base, and a silyl derivative,
- b) conjugating 4-vinyl pyridine to the lactam to form ##STR58## c) alkylating ii-a to form ##STR59## wherein R is C.sub.1-4 alkyl or benzyl.
Dependencies are inferred from the claim text.