These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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. Recommanded Product: trans-Ethyl 4-hydroxycyclohexanecarboxylate
VII) Synthesis of CP30450-3; Ethyl 4-[(/erf-butyldimethylsilyl)oxy]cyclohexanecarboxylate (55); Following protocols reported by Wild,10 a solution of Ethyl 4- hydroxycylohexanecarboxylate (54) (1.0 mL, 6.20 mmol) in DMF (3.0 mL) was treated with imidazole (929 mg, 13.6 mmol) and tert-butyldimethylsilyl chloride (1.22 g, 8.09 mmol) and the resulting mixture stirred magnetically at 18 °C under a nitrogen atmosphere for 20 h. The reaction mixture was then treated with Et2O (50 mL), washed with HCl (1 x 5 mL of a 1 M aqueous solution), then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (hexane- 1:49 v/v ethyl acetate/hexane gradient elution) to afford a ca. 1:1 mixture of the cis- and troens-isomeric forms of the title compound 55 (1.78 g, quant.) as a colourless oil, Rf 0.7 in 3:7 v/v ethyl acetate/hexane.1H NMR (300 MHz) delta 4.12 and 4.11 (2 x q, J 7.1 and 7.1 Hz, 2 x 2H), 3.89 and 3.56 (2 x m, 2 x IH), 2.33-2.16 (complex m, 2 x IH), 1.98-1.87 (complex m, 2 x 2H), 1.68-1.22 (complex m, 2 x 6H), 1.25 and 1.24 (2 x t, J 7.1 and 7.1 Hz, 2 x 3H), 0.88 and 0.87(8) (2 x s, 2 x 9H), 0.05 and 0.03 (2 x s, 2 x 6H).13C NMR (75 MHz) delta 175.8 and 175.7 (2 x C), 70.5 and 66.6 (2 x CH), 60.1 and 60.0 (2 x CH2), 42.2 and 42.0 (2 x CH), 34.8 and 32.8 (4 x CH2), 27.2 and 23.4 (4 x CH2), 25.8 and 25.7(7) (6 x CH3), 18.2 and 18.1 (2 x C), 14.2 (2 x CH3), -4.7 and -4.9 (4 x CH3).
The synthetic route of trans-Ethyl 4-hydroxycyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CRYPTOPHARMA PTY LTD; WO2008/124878; (2008); A1;,
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