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, 2-9 (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 2-10 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-e116231e76f1462e9b80faa332487526

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06410526B1