Ethyl chloroacetate → HCID 58200295, compound

To a stirring mixture of NaH (900 mg, 37.5 mmol) in THF (25 mL) at room temperature under N2 atmosphere was added dropwise a solution of (R)-2-amino-2-(3-fluoro-phenyl)-ethanol (4.0 g, 26.4 mmol) in THF (25 mL). The reaction mixture was stirred at room temperature for 30 minutes, then cooled to 0° C. A solution of ethyl chloroacetate (3.31 g g, 27 mmol) in THF (10 mL) was added dropwise, and the reaction mixture was stirred for 25 minutes at 0° C., then stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and a 1:1 mixture of brine and water. The organic layer was separated, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 1.73 g (34%) of (R)-5-(3-fluoro-phenyl)-morpholin-3-one, MP=119-121° C.

1. temperaturecooled to 0° C
2. stirringthe reaction mixture was stirred for 25 minutes at 0° C.
3. stirringstirred at room temperature for two hours
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. customthe residue was partitioned between ethyl acetate
6. additiona 1:1 mixture of brine and water
7. customThe organic layer was separated
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was recrystallized from diethyl ether

ORD record

ord-b2ad43bca77948e0991710042a26a6f1

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871760B2