Triethylamine → HCID 19888384, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (14.3 g, 125 mmol) was slowly added to a solution of N-diphenylmethyl azetidin-3-ol (20.0 g, 83.7 mmol) and triethylamine (15.2 g, 151 mmol) in methylene chloride (160 mL) which was maintained at 0° C. by an ice-water bath. After 1.5 hours the slurry was diluted with methylene chloride (160 mL) and ice-water (160 mL). The layers were separated and the organic layer was washed with an ice-water mixture (160 mL), dried (MgSO4), and concentrated in vacuo. A solution of the crude mesylate in dimethylformamide (100 mL) was added dropwise to a slurry of the sodium salt of 2,6-dimethylphenol in dimethylformamide prepared by adding a solution of 2,6-dimethylphenol (15.0 g, 125 mmol) in dimethylformamide to a slurry of sodium hydride (60% oil dispension, 7.20 g, 150 mmol) which had been washed (3×60 mL) with hexane and diluted with dimethylformamide (130 mL). The reaction mixture was warmed at 50° for 42 h, cooled to room temperature and added to 1400 mL of an ice-water mixture. The aqueous slurry was extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with water (100 mL), saturated aqueous sodium chloride (100 mL), dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (silica gel, flash chromatography) eluting with ether/hexane (1:9) to give 15.0 g (52%) of white solid with a melting point of 99°-100° C.

Provenance & Evidence