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Merck
CN

Synthesis of 4-substituted 3,3-difluoropiperidines.

The Journal of organic chemistry (2010-01-07)
Riccardo Surmont, Guido Verniest, Jan Willem Thuring, Gregor Macdonald, Frederik Deroose, Norbert De Kimpe
摘要

Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam. This method was applied to establish the synthesis of N-protected 3,3-difluoroisonipecotic acid, a fluorinated gamma-amino acid. 4-Benzyloxy-3,3-difluoropiperidine was prepared using an analogous methodology and was converted to N-protected 3,3-difluoro-4,4-dihydroxypiperidine, a compound with high potential as a building block in medicinal chemistry.

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Sigma-Aldrich
二氟溴乙酸乙酯, 98%