Reaction #1379918

Reaction equation

sodium bicarbonate

1-benzhydryl-3-hydroxyazetidine

dichloromethane

[bis(2-methoxyethyl)amino]sulfur trifluoride

→

desired product

1-Benzhydryl-3-fluoroazetidine

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONvia addition funnel over a period of about 3 h
2. 2
   workup.ADDITIONThe reaction mixture was added portionwise (with caution) to a large extractor
3. 3
   ExtractionThe mixture was extracted three times with 80 mL of dichloromethane
4. 4
   WashThe combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate solution, water and saturated aqueous brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherPurification by flash chromatography

Procedure

A 250 mL, round bottom flask was charged with 3.0 g (12.5 mmol) of 1-benzhydryl-3-hydroxyazetidine and 80 mL of dichloromethane. To the stirring solution at −78° C. was added 4.6 mL (25 mmol) of [bis(2-methoxyethyl)amino]sulfur trifluoride via addition funnel over a period of about 3 h. The reaction mixture was allowed to warm slowly to ambient temperature overnight. The reaction mixture was added portionwise (with caution) to a large extractor containing water and saturated aqueous sodium bicarbonate solution. The mixture was extracted three times with 80 mL of dichloromethane. The combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate solution, water and saturated aqueous brine, dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography using a Biotage® system (gradient, hexane to 80% ethyl acetate/hexane) afforded the desired product. LC/MS 242.1 (M+1).

Source