title: Enantioselective synthesis of cis-3-fluoropiperidin-4-ol, a building block for medicinal chemistry.
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.
authors: Rigel, Inc., 1180 Veterans Boulevard, South San Francisco, California 94080, USA. sshaw@rigel.com
authors: Simon J
authors: SJ
authors: Shaw
authors: Dane A
authors: DA
authors: Goff
authors: Luke A
authors: LA
authors: Boralsky
authors: Mark
authors: M
authors: Irving
authors: Rajinder
authors: R
authors: Singh
mesh_terms: D000588:Amines / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C584812:1-tert-butyloxycarbonyl-3-fluoropiperidin-4-ol; D000588:Amines; D010880:Piperidines