Triethylamine → 3-Azido-1-benzhydrylazetidine

Participants

Reaction Conditions

Reaction Steps

1-(diphenylmethyl)-3-hydroxyazetidine (5.5 g, 22.98 mmol) was dissolved in acetonitrile (16.5 mL), triethylamine (3.48 g, 34.45 mmol) was added. The reaction mixture was cooled to −10° C., methylsulfonyl chloride (3.16 g, 27.59 mmol) was added dropwise slowly. After completion of dropwise addition, the reaction was performed at 0° C. for 1 h, The resultant reaction liquid was poured into water, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, the filtrate was rotatedly concentrated to dryness to yield a white solid. The resultant white solid was added to N,N-dimethyl formamide (25 mL), sodium azide (5.38 g, 82.73 mmol) was added. The reaction mixture was warmed to 100° C. and the reaction was performed overnight. The resultant reaction liquid was cooled to room temperature, poured into water, extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered; the filtrate was rotatedly concentrated to dryness to yield 1-(diphenylmethyl)-3-azidoazetidine.

Provenance & Evidence