Trifluoroacetic acid → HCID 68702636, compound

In a 10 mL round bottom flask was added tert-butyl (S)-2-((ethoxycarbonyl)methoxy)-1-(3-fluorophenyl)ethylcarbamate (69 mg, 0.2 mmol), dichloromethane (1.5 mL), and trifluoroacetic acid (0.5 mL). The solution was stirred at room temperature overnight then concentrated to dryness. The residue was then dissolved in tetrahydrofuran (2 mL) and subsequently treated with DIEA (0.5 mL) and potassium carbonate (excess) and heated 50° C. for 1 h. Upon cooling to room temperature, the reaction solution was diluted with water (3 mL) and extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated. Purification on silica gel (40% ethyl acetate/hexanes) gave (S)-5-(3-fluorophenyl)morpholin-3-one (37 mg, 95%) as a colorless oil. HPLC-MS calculated for C10H10FNO2 (M+H+) 196.2, found 196.1.

1. concentrationthen concentrated to dryness
2. dissolutionThe residue was then dissolved in tetrahydrofuran (2 mL)
3. additionsubsequently treated with DIEA (0.5 mL) and potassium carbonate (excess)
4. temperatureheated 50° C. for 1 h
5. temperatureUpon cooling to room temperature
6. additionthe reaction solution was diluted with water (3 mL)
7. extractionextracted with ethyl acetate
8. dry with materialThe combined organics were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification on silica gel (40% ethyl acetate/hexanes)

ORD record

ord-5af9d177ffea46f9a432d2ea3f007af3

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431607B2