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J Org Chem. 2013 Sep 6;78(17):8892-7. doi: 10.1021/jo401352z. Epub 2013 Aug 19.

Enantioselective synthesis of cis-3-fluoropiperidin-4-ol, a building block for medicinal chemistry.

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1
Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, USA. sshaw@rigel.com

Abstract

The first enantioselective route to both enantiomers of cis-1-Boc-3-fluoropiperidin-4-ol, a highly prized building block for medicinal chemistry, is reported. An enantioselective fluorination is employed, taking advantage of the methodology reported by MacMillan, which uses a modified cinchona alkaloid catalyst. In studying the fluorination reaction, we have shown that the catalyst can be replaced by commercially available primary amines, including α-methylbenzylamine, with similar levels of enantioselectivity. The piperidinols are readily crystallized to obtain enantiopure material.

PMID:
23957501
DOI:
10.1021/jo401352z
[Indexed for MEDLINE]
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