Ammonia → 3-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridine

Participants

Reaction Steps

(S)-1-Methyl-2-pyridinemethanol was reacted with triphenylphosphine, DEAD and 3-hydroxypyridine according to the procedure outlined in Example 1a The crude product was purified by flash chromatography (2×) using (10% MeOH/CHCl3) to remove the diethyl hydrazine dicarboxylate impurity and give a yellow oil in 31% yield. MS (DCI/NH3) m/e 193 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.32 (t, J=1.5 Hz, 1H), 8.22 (t, J=3 Hz, 1H), 7.24-7.2 (m, 2H), 4.14-4.05 (dd, J=9, 6 Hz, 1H), 4.00-3.93 (dd, J=9, 6 Hz, 1H), 3.243.14 (m, 1H, 2.81-2.7 (m, 1H), 2.54 (s, 3H), 2.44-2.31 (m, 1H, 2.14-2.00 (m, 1H, 1.96-1.71 (m, 3H).

Provenance & Evidence