Dimethyl methylphosphonate → [2-Oxo4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-butyl]-phosphonic acid dimethyl ester

To a stirred solution of dimethyl methylphosphonate (1.9 mL, 17.08 mmol) in THF (20 mL) at −78° C. was added nBuLi (10.94 mL, 17.5 mmol). After 30 minutes, 4-9 (1 g , 4.27 mmol) in THF (5 mL) was added. After 1 hour, the reaction was quenched with saturated NH4Cl (10 mL) and warmed to ambient temperature. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70/25/5 CHCl3/EtOAc/MeOH) to give 4-10 as a yellow oil.

1. waitAfter 1 hour
2. customthe reaction was quenched with saturated NH4Cl (10 mL)
3. additionThe mixture was diluted with ethyl acetate
4. washwashed with sat. NaHCO3, brine
5. dry with materialdried over MgSO4
6. customremoval of the solvent
7. customthe residue was chromatographed (silica gel, 70/25/5 CHCl3/EtOAc/MeOH)

ORD record

ord-7bd1db15ce7d4404ac79c47b98112351

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07056909B2