Synthetic Route of 111300-06-2,Some common heterocyclic compound, 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, molecular formula is C11H21NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A solution of frans-N-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}- formamide in anhydrous THF at 0C may be treated with borane-THF complex in THF (1 M, excess). The reaction may be allowed to come to room temperature and may be monitored by LCMS until the reaction is complete. The reaction may be quenched with MeOH and the solvents may be removed under reduced pressure. The crude product may be purified by flash chromatography using with 1 – 5 % (2N N H3 in MeOH) in DCM to give frans-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]- cyclohexyl}-methyl-amine. The neutral amine may be treated with 2N HCI in diethyl ether and DCM.The volatiles may be removed under reduced pressure and the salt may be triturated with diethyl ether and filtered to provide the title compound. LCMS: m/z 439 [M + 1].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, its application will become more common.
Reference:
Patent; TRANSTECH PHARMA, INC.; GOHIMUKKULA, Devi, Reddy; JONES, David; QABAJA, Ghassan; ZHU, Jeff, Jiqun; COOPER, Jeremy, T.; BANNER, William, Kenneth; SUNDERMANN, Kurt; BONDLELA, Muralidhar; RAO, Mohan; WANG, Pingzhen; GOWDA, Raju, Bore; ANDREWS, Robert, C.; GUPTA, Suparna; HARI, Anitha; WO2011/103091; (2011); A1;,
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