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US 10,106,499 B1Granted
Processes for preparing cyclopenta[b]naphthalenol derivatives and intermediates thereof
AssigneeChirogate International Inc.
InventorsShih-Yi Wei, Shih-Hsun Su
Life of this patent
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Abstract
Novel processes for preparing cyclopenta[b]naphthalenol derivatives of Formula 1 which are useful for the synthesis of corresponding benzindene prostaglandins are provided. The present invention also relates to novel intermediates prepared from the processes.
Claims10
A process for preparing a compound of Formula 1:
- wherein R1 is a single bond, C1-4-alkylene or —CH2O—;
- R2 is C1-7-alkyl, aryl or aralkyl, each of which is unsubstituted or substituted by C1-4-alkyl, halogen or trihalomethyl;
- P2 and P3 are the same or different protecting groups for the hydroxyl groups;
- and is a single bond or a double bond,
- comprising reacting a compound of Formula 2:
- wherein X is a sulfonyl group;
- R1, R2, , P2 and P3 are as defined above, with a base.
4 more elements
A process for preparing a compound of Formula 1:
- wherein R1 is a single bond, C1-4-alkylene or —CH2O—;
- R2 is C1-7-alkyl, aryl or aralkyl, each of which is unsubstituted or substituted by C1-4-alkyl, halogen or trihalomethyl;
- P2 and P3 are the same or different protecting groups for the hydroxyl groups;
- and is a single bond or a double bond,
- comprising the steps of
- (a) sulfonylation of a compound of Formula 3
- in the presence of a first base with a sulfonyl donor to form a compound of Formula 2,
- wherein X is a sulfonyl group;
- R1, R2, , P2 and P3 are as defined above, and
- (b) intramolecular alkylation of the compounds of Formula 2 in the presence of a second base to form the compound of Formula 1.
7 more elements
A compound of Formula 3
- wherein R1 is a single bond, C1-4-alkylene or —CH2O—;
- R2 is C1-7-alkyl, aryl or aralkyl, each of which is unsubstituted or substituted by C1-4-alkyl, halogen or trihalomethyl;
- P2 and P3 are the same or different protecting groups for the hydroxyl groups, and is a single bond or a double bond.
Dependencies are inferred from the claim text.