Triethylamine → HCID 86727641, compound

Participants

Reaction Steps

To a solution of 3-acetyl-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (prepared from 1-(tert-butoxycarbonyl)-3-methylazetidine-3-carboxylic acid using the similar procedure detailed in Preparation #4, Steps A-B, 0.10 g, 0.47 mmol) and triethylamine (0.5 mL, 3.8 mmol) in EtOH (2 mL) was added aqueous hydrazine hydrate (85%, 0.117 g, 2.34 mmol) and the solution was heated at reflux for 4 h. The reaction mixture was cooled to ambient temperature and poured into water. The mixture was extracted with DCM (3×15 mL) and the combined organic phase was washed with brine (10 mL) and concentrated in vacuo to give 3-(1-hydrazono-ethyl)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.076 g, 71%), which was used directly in the next step without further purification. TLC: Rf=0.15 (eluting with 50% EtOAc in petroleum ether).

Provenance & Evidence