Water → HCID 86722596, compound

Participants

Reaction Conditions

Reaction Steps

Cyclopropanecarboxylic acid (600 mg, 6.97 mmol), DMAP (170 mg, 1.39 mmol) and EDC.HCl (1.19 g, 7.67 mmol) were added in that order to a stirred solution of benzyl 2-methylhydrazinecarboxylate hydrochloride (JOC, 2013, 78, 3541-3552.) (1.80 g, 8.37 mmol) in DCE (10 mL) and the reaction mixture was stirred at 25° C. for 12 h. Water was added to the reaction mixture and the mixture extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 30% hexane in EtOAc to afford the title compound as a colourless gum (1.6 g, 80%): 1H NMR (300 MHz, DMSO-d6) δ10.01 (bs, 1H), 7.37 (s, 5H), 5.18 (s, 2H), 2.97 (s, 3H), 1.98-1.89 (m, 1H), 0.70-0.68 (m, 4H); ESIMS m/z 247.0 ([M−H]−); IR (thin film) 3502, 2928, 1736 cm−1.

Provenance & Evidence