Hydrochloric Acid → (3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochloride

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Reaction Steps

To a solution of (3R,4R)-tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate (1.5 g, 5.1 mmol, E-2 from example 46 step E) in methanol (50 mL) under nitrogen was added 12.8 mL of 4 M HCl in dioxane and the reaction was stirred for 1 h at rt. The mixture was then evaporated under reduced pressure to dryness and the residue was washed twice with 20 mL of diethyl ether. The solid residue was dried under vacuum to give (3R,4R)-4-(4-hydroxyphenyl)-piperidin-3-ol hydrochloride E-2a (950 mg, 4.1 mmol). LCMS (method F) RT: 0.17 min, m/z 194 (M+H+). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.74-1.93 (m, 2H) 2.61-2.68 (m, 1H) 2.81-2.93 (m, 1H) 3.21-3.33 (m, 2H) 3.78-3.90 (m, 1H) 6.72 (d, J=8.53 Hz, 2H) 7.00 (d, J=8.53 Hz, 2H) 9.14-9.25 (m, 1H) 9.27-9.44 (m, 1H).

Provenance & Evidence