Acetone → tert-Butyl 3,4-dihydroxypiperidine-1-carboxylate

Beteiligte Stoffe

Reaktionsschritte

To a mixture of tert-butyl 5,6-dihydropyridine-1(2H)-carboxylate (2.40 g, 13.10 mmol, 1 eq) and NMO (2.65 g, 19.60 mmol, 1.5 eq) in acetone (60 mL) was added a solution of OsO4 (20 mg) in isopropanol (5 mL). The mixture was stirred overnight at room temperature. To this, 10 mL of saturated NaHSO3 aqueous solution was added dropwise, the reaction mixture was stirred for 0.5 h at room temperature and concentrated in vacuo. The pH was adjusted to 5-6 by adding dilute hydrochloric acid. The organic phase was extracted with CH2Cl2 (50 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as colorless oil (2.60 g, 92.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 218.2 (M+1).

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