Water → 2[6-[2-(N-Boc-Piperidin-4-yl)ethyl]-(3,4,5,6-tetrahydro-1,1-dioxo-2H-1,2-thiazin-2-yl)]acetaldehyde

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Reaction Steps

To a stirred solution of 89 (0.50 g, 1.29 mmol), THF (16 mL), H2O (12 mL), and NaIO4 (0.69 g, 3.2 mmol) was added OsO4 (1 mL, 0.1 mmol; 2.5 %/tertbutanol) to effect a white precipitate. After 3.0 h, the reaction mixture was diluted with ethyl acetate and washed with H2O, 5% KHSO4, sat. NaHCO3 and brine, dried (MgSO4), and concentrated to give aldehyde 90 as an oil. 1H NMR (400 MHz, CDCl3) δ 9.64 (s, 1H), 4.08 (m, 2H), 4.00 (d, J=17 Hz, 1H), 3.89 (d, J=17 Hz, 1H), 3.62 (m, 1H), 3.14 (m, 1H), 2.96 (m, 1H), 2.66 (m, 2H), 2.20 (m, 1H), 2.08 (m, 1H), 2.00-1.35 (m, 9H), 1.10 (m, 2H).

Provenance & Evidence