Ethyl bromoacetate → Tert-butyl 2-(2-ethoxy-2-oxoethyl)hydrazine-1-carboxylate

Participants

Reaction Steps

Ethyl bromoacetate 3 (6.97 mL, 62.8 mmol) was added to a stirred solution of tert-butylcarbazate 2 (24.9 g, 188.6 mmol) in water (25 mL) at room temperature. The mixture was stirred for 30 min. Water layer was then extracted with ethyl acetate (3×). Ethyl acetate extracts were pooled together and washed with brine. Ethyl acetate was evaporated under vacuum to get crude product which was purified by flash column chromatography using hexane:ethyl acetate (70:30) as an eluent (yield 70%). 1H NMR (500 MHz, CDCl3) 1.28 (3H, CH2—CH3, t), 1.45 (9H, C—CH3, s), 3.64 (2H, NH—CH2—CO, s), 4.20 (2H, CH2CH3, q); MS Anal. Mol. Wt. 218.25 (M+1).

Provenance & Evidence