EP 1725674 A1 20061129 - METHOD FOR THE PRODUCTION OF CHIRAL, SECONDARY ALCOHOLS
Title (en)
METHOD FOR THE PRODUCTION OF CHIRAL, SECONDARY ALCOHOLS
Title (de)
VERFAHREN ZUR HERSTELLUNG VON CHIRALEN, SEKUNDÄREN ALKOHOLEN
Title (fr)
PROCEDE POUR PRODUIRE DES ALCOOLS SECONDAIRES CHIRAUX
Publication
Application
Priority
- EP 2005001977 W 20050225
- AT 4712004 A 20040318
Abstract (en)
[origin: WO2005095628A1] Disclosed is a method for producing chiral, secondary alcohols of formula (I), wherein A represents an aromatic, heterocyclic, or alicyclic ring or a ring system with 4 to 20 C atoms, n represents 0, 1, 2, 3, 4, or 5, R represents halogen, OH, an O-protective group, NO2, N,N-R2,R3 amine, R2 and R3 representing C1-C6 alkyl, phenyl, or benzyl, N,N-R2,R3-amino-C1-C6 alkyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C4 alkoxycarbonyl, or CN, and R1 represents N,N-R2,R3 amine, N,N-R2,R3-amino-C1-C6 alkyl, C1-C12 alkyl, C1-C6-haloalkyl, C1-C4 alkoxycarbonyl, C1-C6 alkoxy-C1-C6 alkyl, or a C2-C5 alkylene radical that forms a ring system along with the A radical. According to the inventive method, a) a ketone of formula (II) is optionally reduced to the corresponding racemic alcohol of formula (III) by means of an aliphatic C1-C6 alcohol in the presence of a transition metal catalyst and a base, and b) the alcohol of formula (III) is reacted to a mixture of (R) ester of formula (IV), wherein R4 represents H or C1-C5 alkyl, and (S) alcohol of formula (I) in the presence of an esterification catalyst and an acyl donor, whereupon the (S) alcohol is isolated from the reaction mixture by means of crystallization or distillation according to the aggregate state thereof.
IPC 8 full level
C12P 41/00 (2006.01); C07C 29/143 (2006.01); C07C 33/46 (2006.01); C12P 7/02 (2006.01)
CPC (source: EP US)
C07C 29/143 (2013.01 - EP US); C12P 7/02 (2013.01 - EP US); C12P 41/004 (2013.01 - EP US); C07B 2200/07 (2013.01 - EP US); Y02P 20/55 (2015.11 - EP US)
Citation (search report)
See references of WO 2005095628A1
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR
DOCDB simple family (publication)
WO 2005095628 A1 20051013; AT 500556 A1 20060115; CN 1934267 A 20070321; EP 1725674 A1 20061129; JP 2007529207 A 20071025; NO 20064686 L 20061218; US 2007196904 A1 20070823
DOCDB simple family (application)
EP 2005001977 W 20050225; AT 4712004 A 20040318; CN 200580008559 A 20050225; EP 05707624 A 20050225; JP 2007503220 A 20050225; NO 20064686 A 20061017; US 59275805 A 20050225