4-[5(R)-Alkyl(or alkenyl)-4(S)-quinuclidin-2(S) or 2(R)-ylcarbon

Details 4-[5(R)-Alkyl(or alkenyl)-4(S)-quinuclidin-2(S) or 2(R)-ylcarbon 4-[5(R)-Alkyl(or alkenyl)-4(S)-quinuclidin-2(S) or 2(R)-ylcarbon

1975-08-20

1978-06-20

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260288CE, 424258, C07D45304

Patent

active

040961460

ABSTRACT:
Quinine, quinidine, their antipodes or racemates and derivatives thereof, are prepared by (a) cyclizing the correspondingly substituted 4-[3-(1-chloro-3(R)-alkyl(or alkenyl)-4-(R)-piperidyl)-1-oxopropyl]quinolines, antipodes or racemates thereof, to the corresponding 4-[5(R)-alkyl(or alkenyl)-4-(S)-quinuclidin-2(S) or 2(R)-ylcarbonyl]quinolines, antipodes or racemates thereof; and (b) stereoselectively reducing the products of step (a) to .sup.a (S)-[5(R)-alkyl(or alkenyl)-4(S)-quinuclidin-2(R)-yl]-4-quinoline-methanols, antipodes or racemates thereof, and .alpha.(R)-[5(R)-alkyl(or alkenyl)-4(S)-quinuclidin-2(S)-yl]-4-quinolinemethanols, antipodes or racemates thereof. Various intermediates and the end products are useful antimalarial and antiarrhythmic agents.

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