Uses
5-Bromo-1,2,3,4-tetrahydroisoquinoline is used to prepare Vaniprevir (MK-7009), a macrocyclic hepatitis C Virus NS3/4a protease inhibitor.
Uses
5-Bromo-1,2,3,4-tetrahydro-isoquinoline, HCl
Synthesis
General procedure for the synthesis of 5-bromo-1,2,3,4-tetrahydroisoquinoline from 5-bromoisoquinoline: 5-bromoisoquinoline (25 g, 120.2 mmol) was dissolved in acetic acid (250 mL). Three equivalents of NaBH4 (13.6 g, 359.5 mmol) were added to the reaction system in batches and the reaction was carried out at room temperature and the progress of the reaction was monitored by LC-MS. Upon completion of the reaction, the pH of the reaction solution was adjusted with saturated aqueous NaHCO3 solution to about 8. Subsequently, the reaction mixture was extracted with ethyl acetate and the organic phases were combined and washed with saturated NaCl solution. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography to afford 5-bromo-1,2,3,4-tetrahydroisoquinoline (10 g, yield: 40%).
References
[1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[2] Patent: CN107540659, 2018, A. Location in patent: Paragraph 0225-0226
