Water → HCID 178514621, compound

To a solution of cis-3-carbomethoxycyclobutylazide (2.8 g, 18.0 mmol) in methanol (8 ml) was added water (8 ml). The resulting cloudy solution was well stirred and treated dropwise (0.5 h) with an aqueous solution of sodium hydroxide (1N, 18.0 ml) at such a rate that the temperature was kept under 28° C. The reaction mixture was stirred at 23° C. for 2 h and the solvents were evaporated in vacuo to a yellow residue which was diluted with water (12 ml). The aqueous solution was washed with ether (2×15 ml), acidified with 1N hydrochloric acid and extracted with dichloromethane (4×30 ml). The organic extracts were combined, washed with water, dried over anhydrous sodium sulfate and concentrated to a colorless oil; 2.29 g, 90%; ir (neat) νmax :2100 (N3) and 1705 cm-1 (C=O of carboxylic acid); 1Hmr (CDCl3) δ:11.88 (1H, s, H of carboxylic acid), 3.8 (1H, m, H-1) and 3.2-2.0 ppm (5H, 2H-2, H-3 and 2H-4).

1. customwas kept under 28° C
2. stirringThe reaction mixture was stirred at 23° C. for 2 h
3. customthe solvents were evaporated in vacuo to a yellow residue which
4. additionwas diluted with water (12 ml)
5. washThe aqueous solution was washed with ether (2×15 ml)
6. extractionextracted with dichloromethane (4×30 ml)
7. washwashed with water
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated to a colorless oil

ORD record

ord-909759bbf2d64fa188daada741767a51

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04378314