5-(1-(2-Methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)pentanoic acid → 4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanoic acid

Participants

Reaction Steps

4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanoic acid was prepared using a procedure analogous to 5-(1-(2-methyl-4-phenylthiazol-5-yl)-2-oxabicyclo[2.2.2]octan-4-yl)pentanoic acid except that 5-(4-(iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazole was replaced with 4-(iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane. The title compound was obtained (0.88 g, 2.2 mmol, 95% yield) as a clear oil. LCMS, [M−H]+=373.1. 1H NMR (500 MHz, CDCl3) δ 7.23 (t, J=8.0 Hz, 1H), 7.17-7.10 (m, 1H), 7.05-6.99 (m, 1H), 6.95 (ddd, J=8.2, 2.5, 0.9 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 3.94 (ddd, J=11.3, 9.9, 3.0 Hz, 1H), 3.84 (s, 2H), 3.67-3.58 (m, 1H), 2.36 (t, J=7.4 Hz, 2H), 2.11-1.99 (m, 5H), 1.91-1.82 (m, 2H), 1.77-1.54 (m, 9H), 1.26-1.16 (m, 2H).

Provenance & Evidence