Resolution of 2-substituted 1,4-benzodioxanes by entrainment

被引：22

作者：

Bolchi, Cristiano ^{[1
]}

Pallavicini, Marco ^{[1
]}

Fumagalli, Laura ^{[1
]}

Rusconi, Chiara ^{[1
]}

Binda, Matteo ^{[1
]}

Valoti, Ermanno ^{[1
]}

机构：

[1] Univ Milan, Ist Chim Farmaceut & Tossicol, I-20131 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 09期

关键词：

D O I：

10.1016/j.tetasy.2007.04.026

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The methyl ester of 1,4-benzodioxane-2-carboxylic acid 1 and the mesylate of 2-hydroxymethyl-1,4-benzodioxane 2 are synthetic intermediates whose enantiomers can be advantageously used to prepare a number of enantiopure 2-substituted 1,4-benzodioxanes from readily accessible (+/-)-1,4-benzodioxane-2-carboxilic acid. We have previously demonstrated the conglomerate nature of the enantiomeric systems of 1 and 2. Herein, we report the resolution of their racemates by preferential crystallization according to an entrainment procedure. In particular, the entrainment resolution of 1 showed good efficiency, which makes the present method a competitive alternative to the classical resolutions of 1,4-benzodioxane-2-carboxylic acid with dehydroabietylamine and para-substituted 1-phenylethylamines that we have recently reported. (C) 2007 Elsevier Ltd. All rights reserved.

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页码：1038 / 1041

页数：4

相关论文

共 19 条

[1] LIPASE-CATALYZED KINETIC RESOLUTION OF (+/-)-2-HYDROXYMETHYL-1,4-BENZODIOXANE [J].

ANTUS, S ;

GOTTSEGEN, A ;

KAJTAR, J ;

KOVACS, T ;

TOTH, TS ;

WAGNER, H .

TETRAHEDRON-ASYMMETRY, 1993, 4 (03) :339-344

[2] Highly efficient resolutions of 1,4-benzodioxane-2-carboxylic acid with para substituted 1-phenylethylamines [J].

Bolchi, C ;

Pallavicini, M ;

Fumagalli, L ;

Marchini, N ;

Moroni, B ;

Rusconi, C ;

Valoti, E .

TETRAHEDRON-ASYMMETRY, 2005, 16 (09) :1639-1643

[3] A short entry to enantiopure 2-substituted 1,4-benzodioxanes by efficient resolution methods [J].

Bolchi, C ;

Fumagalli, L ;

Moroni, B ;

Pallavicini, M ;

Valoti, E .

TETRAHEDRON-ASYMMETRY, 2003, 14 (23) :3779-3785

[4] WB 4101-related compounds.: 2.: Role of the ethylene chain separating amine and phenoxy units on the affinity for α1-adrenoreceptor subtypes and 5-HT1A receptors [J].

Bolognesi, ML ;

Budriesi, R ;

Cavalli, A ;

Chiarini, A ;

Gotti, R ;

Leonardi, A ;

Minarini, A ;

Poggesi, E ;

Recanatini, M ;

Rosini, M ;

Tumiatti, V ;

Melchiorre, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (20) :4214-4224

[5] SHORT AND ENANTIOSELECTIVE SYNTHESES OF (R)-2-HYDROXYMETHYL-1,4-BENZODIOXAN AND (S)-2-HYDROXYMETHYL-1,4-BENZODIOXAN [J].

DELGADO, A ;

LECLERC, G ;

LOBATO, C ;

MAULEON, D .

TETRAHEDRON LETTERS, 1988, 29 (30) :3671-3674

[6] ENZYMATIC RESOLUTION OF 2-HYDROXYMETHYL-1,4-BENZODIOXANES [J].

ENNIS, MD ;

OLD, DW .

TETRAHEDRON LETTERS, 1992, 33 (42) :6283-6286

[7] Practical chemical and enzymatic technologies for (S)-1,4-benzodioxan-2-carboxypiperizine intermediate in the synthesis of (S)-doxazosin mesylate [J].

Fang, QK ;

Grover, P ;

Han, ZX ;

McConville, FX ;

Rossi, RF ;

Olsson, DJ ;

Kessler, DW ;

Wald, SA .

TETRAHEDRON-ASYMMETRY, 2001, 12 (15) :2169-2174

[8]

JACQUES J, 1981, ENANTIOMERS RACEMATE, P188

[9] Novel enzymatic route for kinetic resolution of (±)1,4-benzodioxan-2-carboxylic acid [J].

Kasture, SM ;

Varma, R ;

Kalkote, UR ;

Nene, S ;

Kulkarni, BD .

BIOCHEMICAL ENGINEERING JOURNAL, 2005, 27 (01) :66-71

[10]

Khouili M, 1996, FARMACO, V51, P185