Ozone → Tert-butyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

Participants

Reaction Steps

Ozone was bubbled into a solution of 21-3 (1.5 g, 6.4 mmol) in 2:1 CH3OH/CH2Cl2 (102 mL) at -78° C. After 5 min no starting material remained so oxygen was bubbled through the solution for 15 min to remove excess ozone. NaBH4 (1.7 g, 45 mmol) was added and the cooling bath removed. After 1 h the reaction mixture was concentrated. The residue was diluted with H2O (30 mL) and then extracted with CHCl3 (300 mL). The organic phase was washed with brine (30 mL), dried (MgSO4), and concentrated. Flash chromatography (silica, EtOAc) gave 21-4 as a nearly colorless oil. Rf 0.42 (silica, EtOAc).

Provenance & Evidence