Hydrazine hydrate (1:1) → Tert-butyl 3-hydrazinylazetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 3-iodoazetidine-1-carboxylate (142 g, 0.50 mol) and hydrazine hydrate (245.2 mL, 5.02 mol) were mixed in ethanol (284 mL) and the reaction mixture was heated to 85° C. for 48 hours under nitrogen. The reaction mixture was cooled and the ethanol was removed in vacuo. The residue was partitioned between water (200 mL) and dichloromethane (300 mL), the water layer was re-extracted with dichloromethane (2×200 mL), the combined organics were dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to afford the title compound as a colourless oil (88.37 g). This compound was used immediately in the next step without purification.

Provenance & Evidence