N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide → HCID 89527308, compound

Participants

Reaction Conditions

Reaction Steps

N,3,3-trimethoxy-N-methylcyclobutanecarboxamide (12.19 g, 60.0 mmol) was dissolved in THF (130 mL), cooled to 0° C. and treated with 3-butenylmagnesium bromide (168 mL, 0.5 M/THF, 84 mmol). After stirring for 1.5 h at room temperature, the reaction was re-cooled to 0° C. and quenched with 1 N citric acid (30 mL), diluted with ethyl acetate, washed successively with water, saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5-40% ethyl acetate in heptane to afford the desired product 10.98 g (92%). Rf 0.77 (50% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 5.87-5.72 (m, 1H), 5.06-4.95 (m, 2H), 3.17 (s, 3H), 3.13 (s, 3H), 3.06-2.88 (m, 1H), 2.54-2.48 (m, 2H), 2.38-2.28 (m, 6H).

Provenance & Evidence