2-Methylpyridin-3-ol → 2-methyl-3-(N-t-butoxycarbonyl-2-(R)-azetidinylmethoxy)pyridine

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Reaction Steps

An ice cooled solution of the compound from step 41a (0.151 g, 0.81 mmol) was allowed to react with 2-methyl-3-hydroxypyridine (0.092 g, 0.85 mmol) under the conditions of Example 2a, except that DEAD was replaced by di-t-butyl azodicarbonate, to yield the title compound (0.125 g, 55%). MS (DCI/NH3) m/e: 279 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.11 (dd J=4.6, 1.3 Hz, 1H), 7.20-7.10 (m, 2H), 4.54-4.53 (m, 1H), 4.36-4.35 (m, 1H), 4.09 (dd, J=10.0, 2.6 Hz, 1H), 3.95-3.88 (m, 2H), 2.55 (s, 3H), 2.42-2.30 (m, 2H), 1.40 (s, 9H).

Provenance & Evidence