Uses
1,2,3,4-Tetrahydro-6-isoquinolin-6-ol Hydrobromide is a chemical reagent used in the organic synthesis. Used in the preparation of androgen receptor modulators (SARMs) as well as steroidmimetic and chimeric microtubule disruptors.
Synthesis
General procedure for the synthesis of 1,2,3,4-tetrahydroisoquinolin-6-ol hydrobromide from 6-methoxy-1,2,3,4-tetrahydroisoquinoline: 6-methoxy-1,2,3,4-tetrahydroisoquinoline (2.12 g, 13.0 mmol) was dissolved in 48% aqueous hydrobromic acid. The reaction mixture was stirred at 120°C for 3 hours. After completion of the reaction, the solvent was removed by vacuum concentration. The obtained residue was suspended in ethyl acetate and the solvent was evaporated again to afford 1,2,3,4-tetrahydroisoquinolin-6-ol hydrobromide (2.99 g, 95% yield) as a reddish brown solid. The product was characterized by 1H NMR (300 MHz, D2O): δ 7.10 (d, J = 8.4 Hz, 1H), 6.82-6.75 (m, 2H), 4.28 (s, 2H), 3.48 (t, J = 6.3 Hz, 2H), 3.05 (t, J = 6.3 Hz, 2H).
References
[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 789 - 801
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 12, p. 2208 - 2216
[3] Patent: US6562828, 2003, B1
[4] Patent: US5936089, 1999, A
[5] Patent: WO2007/146122, 2007, A2. Location in patent: Page/Page column 42
