Hydrochloric Acid → HCID 58815950, compound

Participants

Reaction Steps

To a solution of 1-{3-[(R)-((2S,5R)-4-allyl-2,5-dimethyl-piperazin-1-yl)-(3-hydroxy-phenyl)-methyl]-benzoyl}-piperidine-4-carboxylic acid ethyl ester (512 mg, Example 119) in THF (5 mL) was added 1 N NaOH solution (4 mL). The reaction was stirred at room temperature overnight. The reaction solution was neutralized by the addition of 1 N HCl solution (4 mL). The reaction solution was concentrated to dryness under vacuum to give crude product, which was subjected to reverse phase C-18 column chromatography conducted on CombiFlash™ Sq 16×(gradient: 100% H2O to 100% MeOH) to give 1-{3-[(R)-((2S,5R)-4-allyl-2,5-dimethyl-piperazin-1-yl)-(3-hydroxy-phenyl)-methyl]-benzoyl}-piperidine-4-carboxylic acid (445 mg; 92%). 1H NMR (300 MHz, CD3OD) δ 7.52-7.37 (m, 3H), 7.28 (m, 1H), 7.19 (dd, J=8.0, 8.0 Hz, 1H), 6.72 (m, 3H), 5.93 (m, 1H), 5.45 (m, 2H), 5.30 (s, 1H), 4.48 (m, 1H), 3.69 (m, 2H), 3.39 (m, 1H), 3.19-2.99 (m, 4H), 2.79 (m, 2H), 2.65 (m, 1H), 2.47 (m, 1H), 2.13 (m, 1H), 1.98 (m, 1H), 1.79 (m, 1H), 1.64 (m, 2H), 1.27 (d, J=6.0 Hz, 3H), 1.20 (d, J=6.5 Hz, 3H).

Provenance & Evidence