Methanesulfonyl chloride → HCID 24801408, compound

Participants

Reaction Steps

Methanesulfonyl chloride (0.53 mL, 6.8 mmol) was added dropwise to a stirred solution of 9 (530 mg, 2.8 mmol) and Hunig's base (0.986 mL, 5.6 mmol) in CH2Cl2 (10 mL) and left overnight at room temperature. The reaction was then diluted with CH2Cl2 (100 mL) and washed with water (25 mL), brine (25 mL), dried (MgSO4) and concentrated in vacuo. Sodium thiomethoxide (218 mg, 3109 μmol) was added portionwise to a solution of the residue, presumably tert-butyl 3-(methanesulfonyloxymethyl)azetidine-1-carboxylate (550 mg, 73%), in DMF (5 mL) and stirred at room temperature overnight. The reaction was diluted with toluene (100 mL) and washed with water (25 mL), brine (25 mL), dried (MgSO4) and concentrated in vacuo. Chromatography (MeOH/CH2Cl2=5:95) of the resulting residue afforded 13 as an oil (120 mg, 27%). 1H NMR (CDCl3): δ 3.98 (m, 2H), 3.54 (m, 2H), 2.65 (brs, 3H), 2.03 (s, 3H), 1.37 (s, 9H). 13C NMR (CDCl3): δ 155.3, 78.3, 53.1, 37.4, 27.4, 14.5.

Provenance & Evidence