Methyl iodide → Methyl 2-(t-butyloxycarbonyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylate

Temperature

25 °C

To a solution of Methyl 2-(t-butyloxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3(S)-carboxylate (0.615 g, 2.0 mmol) in DMF (7 mL) was added K2CO3 (0.304 g, 2.2 mmol) and iodomethane (0.137 mL, 2.2 mmol). The mixture was stirred for 18 hr at 25° C. Approximately 14% of the starting material remained. An additional amount of iodomethane (0.050 mL) was added and stirring continued for 18 hr. The DMF was evaporated in vacuo and the residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (30 mL). The ethyl acetate layer was washed with saturated NaCl solution (30 mL) and dried (MgSO4). Filtration and evaporation in vacuo gave the title compound.

1. stirringstirring
2. waitcontinued for 18 hr
3. customThe DMF was evaporated in vacuo
4. customthe residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (30 mL)
5. washThe ethyl acetate layer was washed with saturated NaCl solution (30 mL)
6. dry with materialdried (MgSO4)
7. filtrationFiltration and evaporation in vacuo

ORD record

ord-db3eff92bb324ee0a60128be030d298b

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05932590