The origin of a common compound about trans-4-Aminocyclohexanol

With the rapid development of chemical substances, we look forward to future research findings about 27489-62-9.

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 27489-62-9, name is trans-4-Aminocyclohexanol. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of trans-4-Aminocyclohexanol

In a round bottom flask fitted with a condenser, a mixture of 4- aminocyclohexan-1-ol (1.219 g, 10.58 mmol), 2,4-dichlorofuro[3,2-d]pyrimidine (2.000 g, 10.58 mmol), Hunig’s base (2.735 g, 3.686 mL, 21.16 mmol), and iPrOH (26.38 mL) was heated to 100 C for 16 h. The solvent was removed, and the crude residue was partitioned between EtOAc and saturated aqueous NH4Cl. The layers were separated, and the aqueous further extracted with EtOAc (2x). The combined organics were dried (Na2SO4), filtered and concentrated to furnish an orange solid. 1H NMR (CDCl3) shows clean desired 4-[(2-chlorofuro[3,2-d]pyrimidin-4- yl)amino]cyclohexanol (2.659 g, 9.932 mmol, 93.89%) along with residual EtOAc. Dried under vacuum overnight and carried forward as is. 1H NMR (400 MHz, CDCl3) delta 7.73 (d, J = 1.7 Hz, 1H), 6.78 (d, J = 2.1 Hz, 1H), 5.09 (s, 1H), 4.20 – 4.08 (m, 1H), 3.78 – 3.61 (m, 1H), 2.19 (d, J = 11.5 Hz, 2H), 2.05 (d, J = 10.8 Hz, 2H), 1.66 – 1.45 (m, 4H), 1.45 – 1.30 (m, 2H). ESI-MS m/z calc.267.07745, found 268.15 (M+1)+; Retention time: 0.56 minutes.

With the rapid development of chemical substances, we look forward to future research findings about 27489-62-9.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; MAXWELL, John, Patrick; JACKSON, Katrina, Lee; TANG, Qing; MORRIS, Mark, A.; RONKIN, Steven, M.; XU, Jinwang; COTTRELL, Kevin, M.; CHARIFSON, Paul, S.; (280 pag.)WO2019/143678; (2019); A1;,
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