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@inproceedings{557658,
author = {Navrátilová, Hana and Kareš, Radovan and Potáček, Milan},
address = {Gainesville, Florida},
booktitle = {Speaker's Presentation & materials},
keywords = {Microwave-assisted; Elimination},
language = {eng},
location = {Gainesville, Florida},
pages = {8-11},
publisher = {CEM},
title = {Preparation of 4-(4-fluoropheny)-1-methyl-3-methylenepiperidine by Microwave-assisted Elimination Reaction},
year = {2003}
}
TY - JOUR
ID - 557658
AU - Navrátilová, Hana - Kareš, Radovan - Potáček, Milan
PY - 2003
TI - Preparation of 4-(4-fluoropheny)-1-methyl-3-methylenepiperidine by Microwave-assisted Elimination Reaction
PB - CEM
CY - Gainesville, Florida
KW - Microwave-assisted
KW - Elimination
N2 - Paroxetine 1 is an antidepressive drug belonging to a family of selective serotonine-reuptake inhibitors used in the treatment of depression and Parkinsons disease.1,2 The drug is marketed as a hydrochloride in an enantiopure form with the (3S,4R)-configuration under the name of Paxil and Seroxat. trans-4-(4-Fuorophenyl)-3-hydroxymethyl-1-methylpiperidine 2 (Z=OH) is an important racemic intermediate of a paroxetine multi-step synthesis which is subjected to the optical resolution to provide a desirable (3S,4R)-enantiomer and a chiral waste highly enriched in the opposite enantiomer.3 In our communication we report on the initial steps of a suggested route to transform the waste enantiomer (3R,4S)-2 into its antipode. Elimination reaction performed with compounds 2-5 was attempted using microwave irradiation and a solid support4 to yield elimination product 6 that in some cases underwent isomerization to 7 (Scheme). The reaction yield depended on the substrate, the type of solid support, support/substrate ratio and irradiation time. The best results (65.5-71% yield) were obtained with a chloroderivative 3 when alumina impregnated with KF was used as a solid support and the irradiation time ranged from 20 to 40 min.
ER -
NAVRÁTILOVÁ, Hana, Radovan KAREŠ a Milan POTÁČEK. Preparation of 4-(4-fluoropheny)-1-methyl-3-methylenepiperidine by Microwave-assisted Elimination Reaction. In \textit{Speaker's Presentation \&{} materials}. Gainesville, Florida: CEM, 2003, s.~8-11.
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