Morpholine → HCID 90357010, compound

Compound 20 (3.0 g, 13.9 mmol), was dissolved in THF (100 mL). Morpholine (20 mL, 229 mmol) was added and the mixture stirred at reflux for 1 hour. DCM (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL) were added and the layers separated. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was dissolved in EtOH (200 mL) and 10% Pd/C (wet, ˜300 mg) followed by ammonium formate (880 mg, 14.0 mmol) added. The mixture was stirred at reflux for 1 hour. The mixture was cooled to rt, filtered through celite, washing the precipitate with EtOAc. The collected filtrate was diluted with saturated ammonium bicarbonate solution (100 mL) and the layers separated. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was triturated with EtOAc-isohexane to afford the title compound as an off-white solid (2.1 g, 63%); (m/z): 237 [MH]+.

1. temperatureat reflux for 1 hour
2. customthe layers separated
3. dry with materialThe organic phase was dried (MgSO4)
4. filtrationfiltered
5. customthe solvent evaporated in vacuo
6. dissolutionThe residue was dissolved in EtOH (200 mL)
7. additionadded
8. stirringThe mixture was stirred
9. temperatureat reflux for 1 hour
10. filtrationfiltered through celite
11. washwashing the precipitate with EtOAc
12. additionThe collected filtrate was diluted with saturated ammonium bicarbonate solution (100 mL)
13. customthe layers separated
14. dry with materialThe organic phase was dried (MgSO4)
15. filtrationfiltered
16. customthe solvent evaporated in vacuo
17. customThe residue was triturated with EtOAc-isohexane

ORD record

ord-e5463e04a26a4badb67d0ed2119cd9ca

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09433622B2