Triethylamine → (5-Oxo-4-azaspiro[2.4]hept-7-yl)methyl methanesulfonate

Participants

Reaction Steps

Methanesulfonyl chloride (0.40 g, 1.0 mmol) and triethylamine (0.22 mL, 1.6 mmol) were added to a solution of 7-(hydroxymethyl)-4-azaspiro[2.4]heptan-5-one (0.11 g, 0.78 mmol) in DCM (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (10 mL×3). The organic layers were combined and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (neat ethyl acetate, Rf=0.6) to afford (5-oxo-4-azaspiro[2.4]hept-7-yl)methyl methanesulfonate. 1H NMR (400 MHz, CDCl3) δ 5.87 (br s, 1H), 4.35-4.01 (m, 2H), 2.95 (s, 3H), 2.87-2.54 (m, 2H), 2.41-2.35 (m, 1H), 1.05-0.72 (m, 4H).

Provenance & Evidence