Lithium hydroxide, monohydrate → HCID 68710012, compound

Participants

Reaction Steps

To a solution of methyl 1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-4,5-dihydro-1H-pyrrolo[2,3-f]isoquinoline-3-carboxylate E17 (1.4 mmol) in 30 mL of a mixture THF/MeOH/H2O 8:1:1, lithium hydroxide monohydrate (2.8 mmol) was added. The resulting solution was stirred at reflux for 6 h. The solvent was removed, the residue redissolved in water and neutralized with aq KH2PO4. The desired product was extracted with DCM/methanol 9:1 and the organic layer was dried (Na2SO4) and evaporated to give, after trituration with diethylether, the title compound (63% yield). ESI (+) MS: m/z 343 (MH+); MS (ES−) 341. 1H NMR: 1.30-1.55 (m, 6H), 2.79-2.86 (m, 2H), 2.87-2.97 (m, 2H), 3.31-3.51 (m, 2H), 3.68-3.75 (m, 1H), 3.86-3.94 (m, 1H), 4.49-4.57 (m, 3H), 7.63-7.67 (m, 1H), 7.68 (s, 1H), 8.44 (d, J=5.61, 1H), 8.47 (s, 1H), 12.06 (bs, 1H).

Provenance & Evidence