反应详情

A solution of morpholine-4-carboxylic acid [(R)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide (90 mg, 0.19 mmol) in methylene chloride (6 ml) was treated with Dess-Martin periodinane (162 mg, 0.38 mmol). After stirring at room temperature for 2 hours the reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), then with saturated aqueous bicarbonate solution then with water, then dried over Na2SO4 and then evaporated under reduced pressure. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane to give morpholine4-carboxylic acid [(R)-1-(6-oxo-cyclohex-1-enylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide (8 mg). 1H NMR (CDCl3): 9.00 (s, 1H), 7.82 (t, J=5 Hz, 1H), 7.53–7.38 (m, 5H), 6.06 (d, J=6 Hz, 1H), 5.00 (m, 1H), 4.47–4.27 (m, 2H), 3.85 (m, 1H), 3.77–3.62 (m, 4H), 3.48–3.36 (m, 4H), 3.27 (m, 1H), 2.58–2.46 (m, 4H), 2.08–1.97 (m, 2H). MS: 450 (MH+).

1. washwas washed with a solution of Na2S2O3 in water (0.26M)
2. dry with materialwith saturated aqueous bicarbonate solution then with water, then dried over Na2SO4
3. customevaporated under reduced pressure
4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane