Triethylamine → HCID 57542654, compound

Participants

Reaction Steps

To a mixture of (R)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate (32.5 g, 173 mmol) and Et3N (27 mL, 191 mmol) in THF (650 mL) at 0° C. was added methane sulfonylchloride (14.9 ml, 191 mmol) dropwise. The mixture was stirred for 10 min. The precipitation was filtered off and the filtrate was concentrated. The residue was then dissolved with DMF (200 mL). Sodium azide (34 g, 519 mmol) was then added. The mixture was stirred at 65° C. for 6 hours. 300 mL EtOAc and 300 mL brine were then added to the reaction mixture. The organic layer was dried and concentrated. The residue was purified by Biotage silica gel chromatography (EtOAc:Hexane 1:4) to give (R)-tert-butyl 2-(azidomethyl)azetidine-1-carboxylate as a colorless oil (32 g, 87% yield). LRMS (M−100+H+) m/z 113.1.

Provenance & Evidence