Morpholine → HCID 21049007, compound

Participants

Reaction Conditions

Reaction Steps

A solution of morpholine (200 μl, 2.3 mmol) and triethylamine (480 μL, 0.38 mmol) in dichloromethane (1 ml) was added dropwise to a solution of sulfuryl chloride (322 μL, 0.38 mmol) in dichloromethane (2 ml) at 0° C. After 1.25 hours the reaction was diluted with ethyl acetate and H2O, the organic layer washed with 2N HCl, dried (MgSO4) and evaporated to an oil which was taken up in acetonitrile (2 ml) and added to a solution of Intermediate R (100 mg, 0.26 mmol) in acetonitrile (2 ml) at room temperature, followed by Hünig's Base (100 μl, 0.52 mmol). Reaction was heated to 80° C. for 6 hours then diluted with ethyl acetate and washed with 2N sodium hydroxide, dried (MgSO4) and evaporated to a brown oil which was purified by chromatography, eluting with 20% ethyl acetate/hexane to obtain a white solid (38 mg). 1H NMR (360 MHz, CDCl3) δ 7.39–7.30 (4H, m), 7.09–7.04 (2H, m) 6.88–6.81 (1H, m), 4.50–4.48 (1H, d, J=6.6 Hz), 3.76–3.74 (4H, m), 3.58–3.56 (1H, m), 3.22–3.20 (4H, m), 2.43–2.35 (4H, m), 2.04–1.99 (2H, m), 1.57–1.50 (2H, m). m/z=533, 535 [MH]−

Provenance & Evidence