Hydrogen Peroxide → (1R,2S)-2-(3-pyridyl)tetrahydro-2H-thiopyran 1-oxide

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Reaction Steps

A solution of (S)-2-(3-pyridyl)tetrahydro-2H-thiopyran (0.6 g) and copper (II) acetylacetonate (0.8 g) in ethanol (15 ml) is treated with hydrogen peroxide (2 ml; 27.5%), in 0.5 ml portions during a 20 hour period. Two hours after the final addition the reaction mixture is diluted with ethyl acetate (30 ml) and washed with saturated brine (2×30 ml). The combined brine washes are then extracted with ethyl acetate (3×30 ml), the combined ethyl acetate phases are dried over magnesium sulphate, filtered and evaporated under reduced pressure, to give (1R,2S)-2-(3-pyridyl)tetrahydro-2H-thiopyran 1-oxide (0.5 g), in the form of a white solid, m.p. 131° C. [NMR (CDCl3): 8.7(s,2H), 7.7(d,1H); 7.3(s,1H); 3.6(dd,2H); 2.8(t,1H); 2.3-1.5(m,6H). Elemental analysis: C,61.3; H,6.7; N,6.9; S,16.5.%; calculated: C,61.5; H,6.7; N,7.1; S,16.4%.]

Provenance & Evidence