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

Temperature

0 °C

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 1 M solution 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 (3 N), 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.

1. additionAfter the addition
2. customwas removed
3. customThe methanol was evaporated under reduced pressure
4. extractionthe aqueous solution was extracted with ether (2×10 ml)
5. extractionAfter acidification with dilute hydrochloric acid (3 N), the aqueous phase was extracted with dichloromethane (4×25 ml)
6. washthe combined organic extracts washed with water (10 ml), brine (10 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. customEvaporation of the solvent and distillation (bulb to bulb) of the residue under vacuum

ORD record

ord-e81a769dbf634410829a009e4c0c6139

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04272437