Methanesulfonyl chloride → HCID 86658770, compound

Into a 100-mL 3-necked round-bottom flask, was placed a solution of tert-butyl 4-(3-hydroxyazetidin-1-yl)piperidine-1-carboxylate (300 mg, 1.15 mmol, 1.00 equiv, 98%) in dichloromethane (20 mL), TEA (240 mg, 2.33 mmol, 2.00 equiv, 98%). To the resulting mixture was added MsCl (0.6 mg, 0.01 mmol, 4.50 equiv, 98%) dropwise with stirring. The resulting solution was stirred for 2 h at room temperature in an ice/salt bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with dichloromethane (2×50 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride/H2O (1×100 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to yield tert-butyl 4-(3-(methylsulfonyloxy)azetidin-1-yl)piperidine-1-carboxylate as a white solid. MS: 335 (MH+).

1. customInto a 100-mL 3-necked round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 2 h at room temperature in an ice/salt bath
3. customThe reaction was then quenched by the addition of water
4. extractionThe resulting solution was extracted with dichloromethane (2×50 mL)
5. washThe resulting mixture was washed with sodium chloride/H2O (1×100 mL)
6. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-714c3cf17674465bbcc277d634dc30c4

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822447B2