Synthesis 2017; 49(11): 2394-2401
DOI: 10.1055/s-0036-1588733
psp
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Properties of 2-Oxa-6-azaspiro[3.3]heptane Sulfonate Salts

Richard N. S. van der Haas*
a  Mercachem Process Research B.V., Kerkenbos 1013, 6546BB Nijmegen, The Netherlands
,
Jeroen A. Dekker
a  Mercachem Process Research B.V., Kerkenbos 1013, 6546BB Nijmegen, The Netherlands
,
Jorma Hassfeld
b  Bayer Pharma AG, Chemical Development Wuppertal, Friedrich-Ebert-Strasse 217–333, 42117 Wuppertal, Germany   Email: [email protected]
,
Anastasia Hager
b  Bayer Pharma AG, Chemical Development Wuppertal, Friedrich-Ebert-Strasse 217–333, 42117 Wuppertal, Germany   Email: [email protected]
,
Peter Fey
b  Bayer Pharma AG, Chemical Development Wuppertal, Friedrich-Ebert-Strasse 217–333, 42117 Wuppertal, Germany   Email: [email protected]
,
Philipp Rubenbauer
b  Bayer Pharma AG, Chemical Development Wuppertal, Friedrich-Ebert-Strasse 217–333, 42117 Wuppertal, Germany   Email: [email protected]
,
Eric Damen
a  Mercachem Process Research B.V., Kerkenbos 1013, 6546BB Nijmegen, The Netherlands
› Author Affiliations
Further Information

Publication History

Received: 13 December 2016

Accepted after revision: 31 January 2017

Publication Date:
02 March 2017 (online)


Abstract

An improved synthesis of the bicyclic spiro compound 2-oxa-6-azaspiro[3.3]heptane is presented. While this compound is often isolated as an oxalate salt, its isolation as a sulfonic acid salt yields a more stable and more soluble product. With these improved properties access to a wider range of reaction conditions with the spirobicyclic 2-oxa-6-azaspiro[3.3]heptane has been enabled.

 
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