Facile deuteration of chiral N,N'-substituted piperazines

V. Santes; E. Gómez; R. Santillan; N. Farfán

doi:10.1055/s-2001-10810

Facile deuteration of chiral N,N'-substituted piperazines

V. Santes, E. Gómez, R. Santillan, N. Farfán

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

The synthesis of four chiral N,N'-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD₄ or BD₃·THF to afford 2,3-d₂-piperazine and 2,3-dimethyl-2,3-d₂-piperazine, while 2,2,3,3-d₄- and 2,2,3,3,5,6-d₆-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.

Original language	English
Pages (from-to)	235-238
Number of pages	4
Journal	Synthesis (Germany)
Issue number	2
DOIs	https://doi.org/10.1055/s-2001-10810
State	Published - 2001
Externally published	Yes

Keywords

Amino alcohols
Asymmetric synthesis
Bisoxazolidine
Condensation
N,N'-substituted piperazine
Reductions

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10.1055/s-2001-10810

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title = "Facile deuteration of chiral N,N'-substituted piperazines",

abstract = "The synthesis of four chiral N,N'-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD4 or BD3·THF to afford 2,3-d2-piperazine and 2,3-dimethyl-2,3-d2-piperazine, while 2,2,3,3-d4- and 2,2,3,3,5,6-d6-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.",

keywords = "Amino alcohols, Asymmetric synthesis, Bisoxazolidine, Condensation, N,N'-substituted piperazine, Reductions",

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year = "2001",

doi = "10.1055/s-2001-10810",

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journal = "Synthesis (Germany)",

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TY - JOUR

T1 - Facile deuteration of chiral N,N'-substituted piperazines

AU - Santes, V.

AU - Gómez, E.

AU - Santillan, R.

AU - Farfán, N.

PY - 2001

Y1 - 2001

N2 - The synthesis of four chiral N,N'-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD4 or BD3·THF to afford 2,3-d2-piperazine and 2,3-dimethyl-2,3-d2-piperazine, while 2,2,3,3-d4- and 2,2,3,3,5,6-d6-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.

AB - The synthesis of four chiral N,N'-substituted piperazines stereoselectively labelled with deuterium atoms is described. The preparation was accomplished by reduction of norephedrine derived bisoxazolidines with LiAlD4 or BD3·THF to afford 2,3-d2-piperazine and 2,3-dimethyl-2,3-d2-piperazine, while 2,2,3,3-d4- and 2,2,3,3,5,6-d6-piperazine were obtained from a strategically deuterated hydroxyethylenediamine precursor using the same route. In all cases, deuteration of bisoxazolidines proceeded with trans stereoselectivity.

KW - Amino alcohols

KW - Asymmetric synthesis

KW - Bisoxazolidine

KW - Condensation

KW - N,N'-substituted piperazine

KW - Reductions

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U2 - 10.1055/s-2001-10810

DO - 10.1055/s-2001-10810

M3 - Artículo

SN - 0039-7881

SP - 235

EP - 238

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 2

ER -

Facile deuteration of chiral N,N'-substituted piperazines

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Keywords

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