Synlett 2016; 27(15): 2251-2253
DOI: 10.1055/s-0035-1562380
letter
© Georg Thieme Verlag Stuttgart · New York

Preparation of 2-Azabicyclo[2.1.1]hexane Hydrochloride

Haili Liao
a   Pharmaron Beijing Co. Ltd., No. 6 Taihe Road, BDA, Beijing 100176, P. R. of China
,
Aimin Li
a   Pharmaron Beijing Co. Ltd., No. 6 Taihe Road, BDA, Beijing 100176, P. R. of China
,
Xingsong Chen
a   Pharmaron Beijing Co. Ltd., No. 6 Taihe Road, BDA, Beijing 100176, P. R. of China
,
Kun Liang
a   Pharmaron Beijing Co. Ltd., No. 6 Taihe Road, BDA, Beijing 100176, P. R. of China
,
Yang Shen
a   Pharmaron Beijing Co. Ltd., No. 6 Taihe Road, BDA, Beijing 100176, P. R. of China
,
Qingfeng Liang
a   Pharmaron Beijing Co. Ltd., No. 6 Taihe Road, BDA, Beijing 100176, P. R. of China
,
Kewei Xu
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   eMail: siu.michael@gene.com   eMail: huestis.malcolm@gene.com
,
Daniel G. M. Shore
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   eMail: siu.michael@gene.com   eMail: huestis.malcolm@gene.com
,
Elisia Villemure
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   eMail: siu.michael@gene.com   eMail: huestis.malcolm@gene.com
,
Michael Siu*
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   eMail: siu.michael@gene.com   eMail: huestis.malcolm@gene.com
,
Malcolm P. Huestis*
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   eMail: siu.michael@gene.com   eMail: huestis.malcolm@gene.com
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Publikationsverlauf

Received: 12. Mai 2016

Accepted after revision: 04. Juni 2016

Publikationsdatum:
07. Juli 2016 (online)


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Abstract

A batchwise, multigram preparation of 2-azabicyclo-[2.1.1]hexane hydrochloride (1·HCl) was developed, delivering a total of 195 grams of material. The key synthetic step involves an intramolecular displacement of a primary alkyl chloride with a tert-butylsulfinamide to forge the [2.1.1]-bicyclic ring system.

Supporting Information