The cyclopropylmethyl group has been identified as an alternative protecting group for the pyridin-2-(1H)-one functionality. This group offers an orthogonal protection strategy to the use of either methyl, which can be difficult to remove, or benzyl, which is unstable to catalytic hydrogenation. It can be installed using silver carbonate catalysis, is easily removed under mild acidic conditions (e.g. formic acid) and has the advantage of being stable to a variety of chemical conditions including basic hydrolysis, addition of organometallic reagents, metal catalysed coupling reactions and importantly catalytic hydrogenation.

Cyclopropylmethyl as an acid labile protecting group for pyridin-2-(1H)-ones

246th National Meeting (2013)

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