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Novel applications of alkyl fluorides in organic synthesis: Versatile nitrogen protecting groups

✍ Scribed by George Theodoridis

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 214 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)02111-x

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✦ Synopsis

The potential of the 2-fluoroethyl group as a nitrogen protecting group was demonstrated. The stability of alkyl fluorides, such as 2-fluoroethyl, to a variety of reaction conditions, makes them attractive nitrogen protecting groups. The 2-fluoroethyl group was easily introduced, in good yields, by the treatment of the NH group with potassium carbonate and 2-bromo-l-fluoroethane. Reaction of the 2-fluoroethyl group with boron tribromide resulted in the replacement of fluorine by bromine, to give the corresponding 2-bromoethyl group which was easily removed by known methods.

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