Triethylamine → Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a solution of 3-hydroxymethylazetidine-1-carboxylic acid tert-butyl ester (for preparation see: Askew, B., et al., US 20033225106) (0.3 g, 1.60 mmol) in DCM (3 mL) was added Et3N (1 mL, 7.17 mmol), followed by methanesulfonyl chloride (0.5 mL, 6.46 mmol) and the reaction mixture stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, the residue dissolved in DCM and the organic phase washed with saturated sodium bicarbonate (aq.). The organic layer was dried (MgSO4), and concentrated in vacuo to give 3-methanesulfonyloxymethylazetidine-1-carboxylic acid tert-butyl ester (0.36 g, 1.40 mmol, 85%) as an oil which was used in the next step without further purification.

Provenance & Evidence