1,4-Dioxane → HCID 68478946, compound

Participants

Reaction Steps

A solution of (3S,4S)-tert-butyl 4-(4-chlorophenyl)-3,4-dihydroxy-3-methylpiperidine-1-carboxylate (2.08 g, 6.08 mmol) in 4 M HCl in dioxane (30.4 mL, 122 mmol) was stirred at room temperature for 45 minutes. The mixture was concentrated in vacuo, then concentrated from methylene chloride (3×) to remove residual HCl, to yield (3S,4S)-4-(4-chlorophenyl)-3-methylpiperidine-3,4-diol hydrochloride (1.7 g, 6.11 mmol, 100% yield) as a powder. 1H NMR (400 MHz, MeOD4) δ 7.55 (d, J=8.8 Hz, 2H), 7.36 (d, J=8.8 Hz, 2H), 3.42 (m, 1H), 3.29 (m, 1H), 3.05 (d, J=13.2 Hz, 1H), 2.71 (ddd, J=13.2, 4.8 Hz, 1H), 1.97 (dt, J=14.5, 3.1 Hz, 1H), 1.08 (s, 3H); m/z (ES+)=242.1 (M+H)+.

Provenance & Evidence