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Titolo:
Development of an efficient and stereoselective manufacturing route to idoxifene
Autore:
Ace, KW; Armitage, MA; Bellingham, RK; Blackler, PD; Ennis, DS; Hussain, N; Lathbury, DC; Morgan, DO; OConnor, N; Oakes, GH; Passey, SC; Powling, LC;
Indirizzi:
GlaxoSmithKline Pharmaceut, Chem Dev, Tonbridge TN11 9AN, Kent, England GlaxoSmithKline Pharmaceut Tonbridge Kent England TN11 9AN Kent, England
Titolo Testata:
ORGANIC PROCESS RESEARCH & DEVELOPMENT
fascicolo: 5, volume: 5, anno: 2001,
pagine: 479 - 490
SICI:
1083-6160(200109/10)5:5<479:DOAEAS>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
LOW-VALENT TITANIUM; CALMODULIN ANTAGONISM; COUPLING REACTIONS; RECEPTOR-BINDING; MCMURRY REACTION; TAMOXIFEN; ANALOGS; CARBONYLS; OLEFINS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
34
Recensione:
Indirizzi per estratti:
Indirizzo: Bellingham, RK GlaxoSmithKline Pharmaceut, Chem Dev, Old Powder Mills, Tonbridge TN11 9AN, Kent, England GlaxoSmithKline Pharmaceut Old Powder Mills Tonbridge Kent England TN11 9AN
Citazione:
K.W. Ace et al., "Development of an efficient and stereoselective manufacturing route to idoxifene", ORG PROC R, 5(5), 2001, pp. 479-490

Abstract

A literature route to 1-(2-{4-[(E)-1-(4-iodophenyl)-2-phenyl-but-1-enyl]phenoxy}ethyl)pyrrolidine (idoxifene) has been modified to tackle various scale-up issues and provide initial supplies. A new highly efficient, robust, and stereoselective manufacturing route is described in detail. This route involves diastereoselective synthesis of tertiary alcohol (1RS,2SR)-1-(4-iodophenyl)-2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]butan-1-ol by Grignard addition to the ketone 1-(4-iodophenyl)-2-phenyl-1-butanone followed by derivatisation and stereoselective syn elimination to provide idoxifene in excellent yield and geometric purity. Evaluation of a more direct route to idoxifene using a McMurry low-valent titanium coupling reaction is also described.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 18/01/20 alle ore 02:09:28