CsF in organic synthesis. The first and convenient synthesis of enantiopure bisoprolol by use of glycidyl nosylate

被引:16
作者
Kitaori, K
Furukawa, Y
Yoshimoto, H
Otera, J
机构
[1] Daiso Co Ltd, Res Labs, Amgasaki, Hyogo 6600842, Japan
[2] Okayama Univ Sci, Dept Appl Chem, Okayama 7000005, Japan
关键词
D O I
10.1016/S0040-4039(98)00452-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective substitution of glycidyl nosylate with phenols is catalyzed by CsF in the presence of K2CO3 in DMF; this reaction enables the first and convenient synthesis of enantiopure bisoprolol. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3173 / 3176
页数:4
相关论文
共 18 条
[1]   S-[1-(2,3-DIAMINOPHENOXY)]-3'-(N-TERT-BUTYLAMINO)PROPAN-2'-OL - SIMPLIFIED ASYMMETRIC-SYNTHESIS WITH CD AND CHIRAL HPLC ANALYSIS [J].
AIGBIRHIO, F ;
PIKE, VW ;
FRANCOTTE, E ;
WATERS, SL ;
BANFIELD, B ;
JAEGGI, KA ;
DRAKE, A .
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :539-554
[2]   Synthesis and in vitro and in vivo characteristics of an iodinated analogue of the beta-adrenoceptor antagonist carazolol [J].
Dubois, EA ;
vandenBos, JC ;
Doornbos, T ;
vanDoremalen, PAPM ;
Somsen, GA ;
Vekemans, JAJM ;
Janssen, AGM ;
Batink, HD ;
Boer, GJ ;
Pfaffendorf, M ;
vanRoyen, EA ;
vanZwieten, PA .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) :3256-3262
[3]  
HAEUSLER G, 1986, J CARDIOVASC PHARM, V8, pS2
[4]   Stereoselective pharmacokinetics of bisoprolol after intravenous and oral administration in Beagle dogs [J].
Horikiri, Y ;
Suzuki, T ;
Mizobe, M .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1997, 86 (05) :560-564
[5]   ISOLATION OF (S)-2,3-DICHLORO-1-PROPANOL ASSIMILATING BACTERIUM, ITS CHARACTERIZATION, AND ITS USE IN PREPARATION OF (R)-2,3-DICHLORO-1-PROPANOL AND (S)-EPICHLOROHYDRIN [J].
KASAI, N ;
TSUJIMURA, K ;
UNOURA, K ;
SUZUKI, T .
JOURNAL OF INDUSTRIAL MICROBIOLOGY, 1992, 10 (01) :37-43
[6]  
KASAI N, IN PRESS J MOL CAT
[7]  
KLUDER JM, 1989, J ORG CHEM, V54, P1295
[8]   CHARACTERIZATION OF [H-3](+/-)CARAZOLOL BINDING TO BETA-ADRENERGIC RECEPTORS - APPLICATION TO STUDY OF BETA-ADRENERGIC-RECEPTOR SUBTYPES IN CANINE VENTRICULAR MYOCARDIUM AND LUNG [J].
MANALAN, AS ;
BESCH, HR ;
WATANABE, AM .
CIRCULATION RESEARCH, 1981, 49 (02) :326-336
[9]   CsF in organic synthesis. Inversion of secondary mesylates and tosylates [J].
Otera, J ;
Nakazawa, K ;
Sekoguchi, K ;
Orita, A .
TETRAHEDRON, 1997, 53 (40) :13633-13640
[10]   CSF IN ORGANIC-SYNTHESIS - MALONIC ESTER SYNTHESIS REVISITED FOR STEREOSELECTIVE CARBON-CARBON BOND FORMATION [J].
SATO, T ;
OTERA, J .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2627-2629