Sodium Bicarbonate → (S)-1-(3-chloro-2-fluorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol

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Reaction Steps

A solution of (R)-tert-butyl 3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (100 mg) in 20% TFA/CH2Cl2 was stirred at 0° C. for 30 min. The mixture was neutralized by addition of sat'd aq NaHCO3, extracted with CH2Cl2 (3×) and dried over Na2SO4. Evaporation of the solvent gave (S)-1-(3-chloro-2-fluorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (70 mg, 91%), which was used without further purification. 1H NMR (400 MHz, CDCl3): 0.90 (m, 1H), 1.52-1.24 (m, 6H), 1.78 (m, 1H), 1.83 (m, 1H), 1.93 (m, 1H), 2.21 (m, 1 H), 2.40 (m, 1 H), 2.83 (m, 1H), 3.00 (m, 1H), 3.12 (s, 3H), 3.31(m, 2 H), 3.63 (m, 1H), 7.06 (m, 1H), 7.30(m, 1 H), 7.55 (t, 1H). MS (E/Z): 330 (M+H+).

Provenance & Evidence