A convenient method for synthesis of optically active methylphenidate from N-methoxycarbonylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction

被引：46

作者：

Matsumura, Y ^{[1
]}

Kanda, Y ^{[1
]}

Shirai, K ^{[1
]}

Onomura, O ^{[1
]}

Maki, T ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 38期

关键词：

asymmetric synthesis; electrochemical reactions; piperidines; diastereoselection;

D O I：

10.1016/S0040-4020(00)00653-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method to prepare optically active methylphenidate starting from piperidine is described. The method consists of a transformation of N-methoxycarbonylated piperidine to the corresponding alpha-methoxylated carbamate utilizing electrochemical oxidation followed by the coupling reaction with optically active Evans imides to produce optically active methylphenidate derivatives with high stereoselectivity (erythrolthreo=5.3/94.7, the three isomer; 99.6%ee). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7411 / 7422

页数：12

共 28 条

[1] A stereoselective synthesis of dl-threo-methylphenidate:: Preparation and biological evaluation of novel analogues [J].

Axten, JM ;

Krim, L ;

Kung, HF ;

Winkler, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9628-9629

[2] Enantioselective synthesis of D-threo-methylphenidate [J].

Axten, JM ;

Ivy, R ;

Krim, L ;

Winkler, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) :6511-6512

[3]

BARLEY RA, 1977, J CHILD PSYCHOL PSYC, V18, P137

[4] Highly regio-, diastereo-, and enantioselective C-H insertions of methyl aryldiazoacetates into cyclic N-BOC-protected amines.: Asymmetric synthesis of novel C2-symmetric amines and threo-methylphenidate [J].

Davies, HML ;

Hansen, T ;

Hopper, DW ;

Panaro, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) :6509-6510

[5] Synthesis and pharmacology of potential cocaine antagonists .2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs [J].

Deutsch, HM ;

Shi, Q ;

GruszeckaKowalik, E ;

Schweri, MM .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (06) :1201-1209

[6] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[7] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[8] STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS [J].

EVANS, DA ;

RIEGER, DL ;

BILODEAU, MT ;

URPI, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1047-1049

[9] DIASTEREOSELECTIVE ADDITION-ELIMINATION REACTIONS OF LITHIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH 2-METHYLENE-3-PHENOXYALKANOATES [J].

KANNO, H ;

OSANAI, K .

TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1503-1506

[10] A convenient method for synthesis of enantiomerically enriched methylphenidate from N-methoxycarbonylpiperidine [J].

Matsumura, Y ;

Kanda, Y ;

Shirai, K ;

Onomura, O ;

Maki, T .

ORGANIC LETTERS, 1999, 1 (02) :175-178

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