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

HRID 1584274Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:22])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:22][CH3:23])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-db3eff92bb324ee0a60128be030d298b
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932590

Reaction notes

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