1-Aminocyclopropane-1-carboxylic acid → 5-(3-Methoxy-2-methylphenyl)-6-oxa-4-azaspiro[2.4]hept-4-en-7-one

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Reaction Steps

To a stirred solution of 1-aminocyclopropanecarboxylic acid (1.06 g, 10.5 mmol) in pyridine (20 mL) cooled to ˜5° C., solid 3-methoxy-2-methylbenzoyl chloride (4.35 g, 23.6 mmol) was added. The mixture was stirred at room temperature for 1 week and evaporated under reduced pressure to leave an oily solid. This material was taken up in 20% ether in hexanes (175 mL), washed with water (50 mL), 5% aqueous HCl (2×50 mL) and saturated aqueous NaHCO3 (50 mL). The organic layer was dried over MgSO4 and evaporated under reduced pressure to leave 5-(3-methoxy-2-methyl-phenyl)-6-oxa-4-aza-spiro[2.4]hept-4-en-7-one (1.90 g) as a yellow solid. 1H NMR (CDCl3) δ (ppm): 1.80 (m, 2H), 1.90 (m, 2H), 2.49 (s, 3H), 3.85 (s, 3H), 7.01 (d, 1H), 7.22 (t, 1H), 7.40 (d, 1H).

Provenance & Evidence