Morpholine → (1-Methyl-2-morpholin-4-yl-ethyl)-carbamic acid tert-butyl ester

To a solution of methanesulfonic acid 2-tert-butoxycarbonylamino-propyl ester (23 mmol) in CH3CN (20 mL) was added morpholine (28 mmol) and K2CO3 (23 mmol) at room temperature. The reaction mixture was brought to 50° C. and kept at the same temperature overnight. The reaction mixture was cooled and solvent was removed under reduced pressure, and the residue was treated with CH2Cl2 (50 mL) and H2O (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4. Solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate) to afford (1-methyl-2-morpholin-4-yl-ethyl)-carbamic acid tert-butyl ester as viscous liquid, yield: 62%. MS (M+H)=245.

1. customwas brought to 50° C.
2. customkept at the same temperature overnight
3. temperatureThe reaction mixture was cooled
4. customsolvent was removed under reduced pressure
5. additionthe residue was treated with CH2Cl2 (50 mL) and H2O (50 mL)
6. customThe organic layer was separated
7. extractionthe aqueous layer was extracted with CH2Cl2
8. dry with materialThe combined organic layer was dried over Na2SO4
9. customSolvent was removed under reduced pressure
10. customthe residue was purified by column chromatography (ethyl acetate)

ORD record

ord-e260e7b98c3d47bba885e9638fca8d6f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841336B2