The synthetic route of 50910-54-8 has been constantly updated, and we look forward to future research findings.
Application of 50910-54-8 , The common heterocyclic compound, 50910-54-8, name is trans-4-Aminocyclohexanol hydrochloride, molecular formula is C6H14ClNO, its 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.
EXAMPLE 51 iV-(4-^ralpha?5-HvdroxycvclohexyI)-./V-methyl-f24i31-benzoxadiazole-5-carboxaniiderra?5-4-aminocyclohexanol hydrochloride (60.6 g, 0.40 mol) and NaHCO3 (14Og) were dissolved in water (700 ml). Ethyl acetate (500 ml) was added and the mixture stirred rapidly using a mechanical stirrer whilst a solution of ethyl chloroformate (48 ml) in ethyl acetate (200 ml) was added slowly. The mixture was stirred overnight and then ethyl acetate (1 1) and water (500 ml) were added to dissolve the precipitate. The aqueous was extracted with ethyl acetate (2×500 ml) and the combined organic phases were washed with 2N HCl, dried over Na2SO4, and the solvent evaporated, to give a white solid (73.7g). This material was dissolved in dry THF (600 ml) and the solution slowly (~ Ih) added to a suspension OfLiAlH4 (29.6g) in THF (600 ml). After stirring overnight at 20C the mixture was cooled in an ice bath and a solution of sodium hydroxide (77g) in water (50 ml) was slowly added. After Ih, some celite was added and the mixture was filtered and washed with dichloromethane. The filtrate was dried (MgSO4) and evaporated under vacuum to give tra?s-4-methylaminocyclohexanol a white solid (45.9g). ;r¡ã?s-4-Methylaminocyclohexanol (37.1g, 0.28 mol), [2,l,3]-benzoxadiazole-5-carboxylic acid (42.7g, 0.26 mol), DMAP (32g, 0.26 mol), HOBT (1 Ig, 0.08 mol) and triethylamine (54 ml) were dissolved in dichloromethane (750 ml) and after 15 minutes, EDCI (10Og, 0.52 mol) was added and the mixture refluxed for 2h. The mixture was washed with 2N HCl (500 ml) and NaHCO3 solution (500 ml), dried over MgSO4 and then concentrated under vacuum. The residue was chromato graphed on silica gel using ethyl acetate/chloroform (3:1) as eluant to give the title product as a white solid (37g) after trituration with ethyl acetate. Mp = 170- 171C, LC-MS, MH+ = 276; 1H NMR (300 MHz, CDCl3, rotamers) delta 7.92 (d, J = 9.0 Hz, IH); 7.82 (s, IH); 7.40 (d, J = 9.0 Hz, IH); 4.60-4.40 and 3.70-3.40 (m, 2H); 2.99 and 2.87 (s + s, 3H); 2.20-1.05 ppm (s, 8H).
The synthetic route of 50910-54-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CORTEX PHARMACEUTICALS, INC.; WO2008/143963; (2008); A1;,
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