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  4. Asymmetric Synthesis. 39.1 Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine
 
research article

Asymmetric Synthesis. 39.1 Synthesis of 2-(1-Aminoalkyl)piperidines via 2-Cyano-6-phenyl Oxazolopiperidine

Froelich, Olivier
•
Desos, Patrice
•
Bonin, Martine
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1996
The Journal of Organic Chemistry

The asym. synthesis of a series of 2-piperidinealkanamines starting from (-)-2-cyano-6-phenyloxazolopiperidine was [i.e., [3R-(3alpha ,5beta ,8abeta )]-hexahydro-3-phenyl-5H-oxazolo[3,2-a]pyridine-5-carbonitrile] (I) as described. LiAlH4 redn. of I followed by hydrogenolysis gave (-)-2-piperidinemethanamine dihydrochloride (II). Addn. of lithium derivs. to the cyano group of I resulted in the formation of intermediate imino bicyclic systems which could be diastereoselectively reduced to substituted diamino alcs. The addn. of an excess of PhLi to I in the presence of LiBr gave a disubstituted amine, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine. [on SciFinder (R)]

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Type
research article
DOI
10.1021/jo960910s
Author(s)
Froelich, Olivier
Desos, Patrice
Bonin, Martine
Quirion, Jean-Charles
Husson, Henri-Philippe
Zhu, Jieping  
Date Issued

1996

Published in
The Journal of Organic Chemistry
Volume

61

Issue

19

Start page

6700

End page

6705

Subjects

Asymmetric synthesis and induction (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile)

•

piperidinemethanamine asym synthesis; aminomethyl piperidine asym synthesis

Note

CAN 125:247551

27-16

Heterocyclic Compounds (One Hetero Atom)

Faculte des Sciences Pharmaceutiques et Biologiques,Universite Rene Descartes,Paris,Fr.

Journal

written in English.

88056-92-2 Role: RCT (Reactant), RACT (Reactant or reagent) (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile); 153918-98-0P; 156350-14-0P; 181872-15-1P; 181872-19-5P; 181872-20-8P; 181872-21-9P; 181872-22-0P; 181872-23-1P; 181872-24-2P; 181872-26-4P; 181872-28-6P; 181872-29-7P; 181872-31-1P; 181872-32-2P; 181872-33-3P; 182074-39-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile); 126811-36-7P; 153918-99-1P; 181872-10-6P; 181872-12-8P; 181872-17-3P; 181872-25-3P; 181872-27-5P; 181872-30-0P; 181872-34-4P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of piperidinealkanamines from (phenyl)oxazolopyridinecarbonitrile)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58560
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