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HERO ID
7444046
Reference Type
Journal Article
Title
Short synthesis of methylphenidate and its p-methoxy derivative
Author(s)
Dias, LC; Fernandes, AMAD
Year
2000
Is Peer Reviewed?
1
Journal
Synthetic Communications
ISSN:
0039-7911
Publisher
Marcel Dekker Inc.
Volume
30
Issue
7
Page Numbers
1311-1318
Language
English
DOI
10.1080/00397910008087153
Web of Science Id
WOS:000086376000018
URL
http://www.tandfonline.com/doi/abs/10.1080/00397910008087153
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Abstract
A short method for the preparation of racemic threo- and erythromethylphenidate derivatives is described. Condensation between α- ethoxy carbamate 1 and silyl ketene acetals 2a-b in the presence of TESOTf (20 mol%) afforded a 1.5:1 mixture of carbamates 3a-b/4a-b. Hydrogenolysis in EtOH followed by treatment with 3N HCl/MeOH afforded the corresponding hydrochlorides 7a-b/8a-b in good yields.
Keywords
2 (1 methyloxycarbonyl 1 phenylmethyl)hexahydropyridinium chloride; 2 [1 (4 methoxyphenyl) 1 methyloxycarbonylmethyl]hexahydropyridinium chloride; acetal derivative; carbamic acid derivative; central stimulant agent; methylphenidate; pyridinium derivative; unclassified drug; article; chemical reaction; drug synthesis; isomer; racemic mixture; reaction analysis; stoichiometry
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