Downstream synthetic route of 7-Nitro-1,2,3,4-tetrahydroisoquinoline

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO126,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (33.1) (4 g, 22.44 mmol) in THF (100 mL) was added TEA (2.27 g, 22.45 mmol) and tert-butoxycarbonyl tert-butyl carbonate (5.4 g, 24.74 mmol) . The reaction mixture was stirred at room temperature for 2h. TLC showed the reaction was complete. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (DCM) to afford tert-butyl 7-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate (33.2) as a yellow liquid (4.4 g, 70.4%). [00535] LCMS: 279.1 [M+1]+. [00536] 1HNMR (400 MHz, CDCl3): delta 1.50 (s, 9H), 2.93 (t, 2H), 3.69 (t, 2H), 4.66 (s, 2H), 7.29 (t, 1H), 8.03-8.02 (m, 2H).

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem