Methyl iodide → HCID 58911620, compound

To a solution of the title compound of Example 215 (23.0 mg, 0.0965 mmol) in dimethylformamide (0.75 mL) were added cesium carbonate (94 mg, 0.29 mmol) and methyl iodide (0.0072 mL, 0.12 mmol). After 4.5 h, the reaction was partitioned between dichloromethane (2 mL) and water (2 mL). The aqueous layer was extracted with dichloromethane (2 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The residue was taken up in a minimum amount of 50% aqueous methanol and loaded onto a methanol-activated water-equilibrated 1-g SCX-type cation exchange column. The column washed with water (6 mL) and 50% aqueous methanol (6 mL). The column was eluted with 2N methanolic ammonia (8 mL). This fraction was concentrated in vacuo to provide (−)-1,2,3,4,11,11a-hexahydro-2-methyl-pyrazino[1,2-b][1,2]benzothiazine 6,6-dioxide as a white solid (19 mg, 79%): LCMS (pos. ion spectrum) m/z 253.

1. customthe reaction was partitioned between dichloromethane (2 mL) and water (2 mL)
2. extractionThe aqueous layer was extracted with dichloromethane (2 mL)
3. dry with materialThe combined organic layers were dried (sodium sulfate)
4. concentrationconcentrated in vacuo
5. washThe column washed with water (6 mL) and 50% aqueous methanol (6 mL)
6. washThe column was eluted with 2N methanolic ammonia (8 mL)
7. concentrationThis fraction was concentrated in vacuo

ORD record

ord-92fd5248e3a94e1d9e09a90a19ec6874

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812024B2