Hydrochloric Acid → Tert-butyl 4-(1,3-dihydroxypropan-2-yl)piperidine-1-carboxylate

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Reaction Conditions

Reaction Steps

To a solution of 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)malonic acid diethyl ester (14.6 g, 0.043 mol) in anhydrous THF (100 mL) and anhydrous toluene (100 mL), LiBH4 (2.1 g. 0.96 mol) was added portion wise. The resulting mixture was heated at 60° C. for 17 h, then stirred at ambient temperature for 24 h. The reaction mixture was slowly added to aqueous HCl (0.1 M, 350 mL) and then extracted with EtOAc. The organic layer was separated and washed with brine, then dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, EtOAc: MeOH 100:0 to 98:2 to 95:5 to 90:10 to 80:20) to afford the title compound as a colourless oil (6.91 g, 63%). 1H NMR (CDCl3, 400 MHz) δ 3.90-3.75 (m, 4H); 2.75-2.58 (m, 4H); 1.77-1.61 (m, 4H); 1.52 (m, 1H); 1.45 (s, 9H) and 1.26-1.13 (m, 1H).

Provenance & Evidence