Morpholine → HCID 19434058, compound

To a solution of the product from Step C (0.79 g, 3.42 mmol) and triethylamine (1.04 g, 10.3 mmol) in anhydrous THF (30 mL) at ambient temperature was added methanesulfonic anhydride (0.89 g, 5.13 mmol) with stirring. After 30 min morpholine (2 mL) was added and the mixture stirred for 1 h at ambient temperature and then heated at reflux temperature for 1 h. The volatiles were evaporated and a saturated aqueous solution of sodium bicarbonate (80 mL) was added. This mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried (MgSO4) and evaporated to give a viscous oil which was purified by column chromatography (silica, 30 to 50% ethyl acetate/hexane) to give a white solid (0.82 g, 84%): mp 104°-106° C.

1. stirringthe mixture stirred for 1 h at ambient temperature
2. temperatureheated
3. temperatureat reflux temperature for 1 h
4. customThe volatiles were evaporated
5. additiona saturated aqueous solution of sodium bicarbonate (80 mL) was added
6. extractionThis mixture was extracted with ethyl acetate (2×100 mL)
7. dry with materialthe combined extracts were dried (MgSO4)
8. customevaporated
9. customto give a viscous oil which
10. customwas purified by column chromatography (silica, 30 to 50% ethyl acetate/hexane)

ORD record

ord-9f0b847734e44677aeb7a16d8bed7493

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05538966