WO1995032178 ENANTIOSELECTIVE PREPARATION OF OPTICALLY PURE ALBUTEROL

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Publication Number WO/1995/032178

Publication Date 30.11.1995

International Application No. PCT/US1995/006539

International Filing Date 23.05.1995

Chapter 2 Demand Filed 18.12.1995

IPC

CPC

Applicants

SEPRACOR, INC. [US]/[US]

Inventors

GAO, Yun
ZEPP, Charles, Melvyn

Agents

TULLEY, Douglas, H., Jr.
TULLEY, Douglas H.,Jr.

Priority Data

08/247,302		23.05.1994		US
08/376,072		20.01.1995		US

Publication Language English (en)

Filing Language English (EN)

Designated States

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Title

(EN) ENANTIOSELECTIVE PREPARATION OF OPTICALLY PURE ALBUTEROL

(FR) PREPARATION ENANTIOSELECTIVE D'ALBUTEROL OPTIQUEMENT PURE

Abstract

(EN) The invention relates to a method for producing albuterol by the resolution of a mixture of enantiomers of 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate using di-toluoyltartaric acid. The invention further relates to a method for producing albuterol by the resolution of a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-(phenylmethoxy)benzoate or $g(a)-[[(1,1-dimethylethyl)amino]methyl]-4-(phenylmethoxy)-1,3-benzenedimethanol using a chiral acid such as (+/-) di-toluoyltartaric acid or (+/-) di-benzoyltartaric acid.

(FR) L'invention concerne un procédé permettant de produire de l'albutérole par dédoublement d'un mélange d'énantiomères de 5-[2-[(1,1-diméthyléthyl)amino]-1-hydroxyéthyl]-2-hydroxybenzoate au moyen d'acide ditoluoyltartrique. L'invention concerne en outre un procédé permettant de produire de l'albutérole par dédoublement d'un mélange d'énantiomères de méthyl5-[2-[(1,1-diméthyléthyl)amino]-1-hydroxyéthyl]-2-(phénylméthoxy)benzoate ou $g(a)-[[(1,1-diméthyléthyl)amino]méthyl-4-(phénylméthoxy)-1,3-benzénediméthanol au moyen d'un acide chiral tel que l'acide (+/-) ditoluoyltratrique ou l'acide (+/-) dibenzoyltartrique.

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
213	Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
10	Separation; Purification; Stabilisation; Use of additives

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
213	Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
10	Separation; Purification; Stabilisation; Use of additives

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
213	Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
213	Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
10	Separation; Purification; Stabilisation; Use of additives

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
C	ACYCLIC OR CARBOCYCLIC COMPOUNDS
215	Compounds containing amino and hydroxy groups bound to the same carbon skeleton
46	having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
56	with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
58	with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
60	the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

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1. WO1995032178 - ENANTIOSELECTIVE PREPARATION OF OPTICALLY PURE ALBUTEROL