Sodium Hydroxide → (1R,2R)-2-(Azidomethyl)cyclopropane-1-carboxylic acid

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Reaction Conditions

Reaction Steps

A solution of trans-ethyl-2-azidomethyl-1-cyclopropane carboxylate (7.282 g, 37.13 mmol) in a mixture of methanol (20 ml) and water (10 ml) was cooled to 0° C. and treated dropwise with 40.8 ml of 1M sodium hydroxide in water (40.8 mmol). After the addition was completed the bath was removed and the solution was stirred at room temperature for 3 h. The methanol was evaporated under reduced pressure and the aqueous solution was extracted with ether (2×10 ml). After acidification with dilute hydrochloric acid (3N), the aqueous phase was extracted with dichloromethane (4×25 ml) and the combined organic extracts washed with water (10 ml), brine (10 ml) and dried over anhydrous sodium sulfate. Evaporation of the solvent and distillation (bulb to bulb) of the residue under vacuum gave 4.830 g (92%) of a clear oil; bp 100°-108° C./0.6 mm Hg (air bath temperature); ir (film) νmax : 2095 (N3), 1695 cm-1 (C=O); 1Hmr (CDCl3) δ: 3.25 (2H, d, J=6, CH2N3), 2.0~0.6 (4H, m, cyclopropyl), 12.3 (1H, s, COOH). Anal. calcd for C5H7N3O2 : C 42.55, H 5.00, N 29.77; Found: C 42.55, H 4.89, N 29.75.

Provenance & Evidence