Synthetic Route of 40571-86-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.40571-86-6, name is Trans-2-(benzylamino)cyclohexanol, molecular formula is C13H19NO, molecular weight is 205.2961, as common compound, the synthetic route is as follows.
B. (S)-Mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol (3) and (R)-Mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol (ent-3): A 1-L single-necked, roundbottomedflask containing equipped with a mechanical stirrer and apressure-equalising addition funnel was charged with the preparedethyl acetate solution (300 mL) containing amino alcohol rac-2, and asolution of (S)-mandelic acid (70.4 g, 0.46 mol, 0.5 equiv.) in EtOAc(150 mL) was added via the addition funnel over a period of 2 h atroom temperature. After the addition was complete the droppingfunnel was rinsed with EtOAc (2 ¡Á 5 mL) and the reaction mixture wasstirred overnight at ambient temperature, followed by 5 h at 0 C. Theprecipitated ammonium salt was collected by suction filtration, washedwith ethyl acetate (2 ¡Á 50 mL), and dried under reduced pressure at roomtemperature over 1 h to afford the (S)-mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol (3) as a colourless solid (131.8 g,0.37 mol), yield 80% based on mandelic acid, m.p. 147-149 C (lit.10146 C); [alpha]D25 = +14.7 (c = 2.0, CHCl3); 1H NMR (CDCl3) delta 0.96-1.29(m, 4 H), 1.58-1.73 (m, 3 H), 1.90 (d, J = 12.6 Hz, 1 H), 2.53 (dt, J = 4.0,J = 12.0 Hz, 1 H), 3.03 (dt, J = 4.3, 10.6 Hz, 1 H), 3.46 (d, J = 12.9 Hz, 1H), 3.89 (d, J = 12.6 Hz, 1 H), 4.90 (s, 1 H), 7.19-7.35 (m, 8 H), 7.49-7.52(m, 2H). The filtrate from the above procedure was concentrated underreduced pressure to give a pale yellow oily residue (518.2 g) which wasdissolved in EtOAc (200 mL), transferred into a 1-L flask, and treatedwith a solution of (R)-mandelic acid ((70.4 g, 0.46 mol, 0.5 equiv.) inethyl acetate (100 mL) similar to the above described procedure, todeliver the (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol (ent-3) as a colourless solid (132.8 g, 0.36 mol), yield 78%based on mandelic acid), [alpha]D25 = -15.3 (c = 2.0, CHCl3). The analyticaldata were in accordance with those observed for the correspondingenantiomer of opposite configuration.
The chemical industry reduces the impact on the environment during synthesis 40571-86-6, I believe this compound will play a more active role in future production and life.
Reference:
Article; Xue, Feng; Li, Chang-Gong; Zhu, Yong; Lou, Tian-Jun; Journal of Chemical Research; vol. 38; 5; (2014); p. 322 – 324;,
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