tert-Butyl acrylate → 3-{4-[4-(4-Piperidin-1-yl-3-trifluoromethyl-phenoxymethyl)-phenyl]-piperidin-1-yl}-propionic acid

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Reaction Steps

Mitsunobu coupling of 4-(4-hydroxymethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester and 4-Piperidin-1-yl-3-trifluoromethyl-phenol, followed by: Boc deprotection, alkylation with t-butyl acrylate, t-butyl ester deprotection, and final RP LC-MS purification as described in a previous example gave 3-{4-[4-(4-piperidin-1-yl-3-trifluoromethyl-phenoxymethyl)-phenyl]-piperidin-1-yl}-propionic acid as a tan solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.25 (bs, 1H), 7.49 (d, 1H), 7.41 (d, 2H), 7.27 (d, 2H), 7.30-7.20 (m, 2H), 5.10 (s, 2H), 3.61-3.52 (m, 2H), 3.36-3.26 (m, 2H), 3.14-3.02 (m, 2H), 2.90-2.80 (m, 3H), 2.78-2.72 (m, 4H), 2.03-1.94 (m, 4H), 1.65-1.55 (m, 4H), 1.53-1.45 (m, 2H); MS (ES+): (491.2, M+1)+.

Provenance & Evidence