* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With iodine; zinc In tetrahydrofuran for 5 h; Heating / reflux
Reference Example 61; (1-Hydroxycyclohexyl) ethyl acetate; To a solution of cyclohexanone (9.52 g, 97.0 mmol), a zinc powder (7.6 g, 116.4 mmol) and a small amount of iodine in THF (100 ml) was added dropwise ethyl bromoacetate (11.8 ml, 106.7 mmol) under a nitrogen atmosphere, and the mixture was heated under reflux for 5 hrs. 10percent Sulfuric acid (100 ml) was carefully added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgS04, and concentrated under reduced pressure to give the title compound (17.2 g, 94percent) as a colorless oil. 1H-NMR (CDCl3) No.: 1 . 27 (3H, t, J=7.0 Hz) , 1.35-1.71 (10H, m), 2.46 (2H, s), 3.43 (lH, s), 4.17 (2H, q, J=7.4 Hz).
Reference：
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[3] Patent: WO2005/105802, 2005, A1, . Location in patent: Page/Page column 127
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[40] Patent: WO2008/106139, 2008, A1, . Location in patent: Page/Page column 470
2
[ 108-94-1 ]
[ 105-39-5 ]
[ 5326-50-1 ]
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3
[ 6975-17-3 ]
[ 5326-50-1 ]
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4
[ 27262-60-8 ]
[ 5326-50-1 ]
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5
[ 108-94-1 ]
[ 141-78-6 ]
[ 5326-50-1 ]
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To a solution of X4 (510 mg) in MeOH was added IN aqueous NaOH. The reaction mixture was stirred at 600C for Ih5 and then concentrated in vacuo. The residue was diluted with water, washed with Et2O and the aqueous layer acidified with IN aqueous citric acid and extracted with EtOAc. The organics were dried (MgSO4) and concentrated in vacuo to yield after recrystallization compound X5 (220mg): 1H-NMR (CDCl3, 500MHz) 3.63 (s, IH), 2.45 (s, 2H), 1.22-1.64 (m, 10H) ppm; FIA m/z 157.2 ES".
[0338] To a solution of X4 (510 mg) in MeOH was added IN aqueous NaOH. The reaction mixture was stirred at 6O0C for Ih, and then concentrated in vacuo. The residue was diluted with water, washed with Et2O and the aqueous layer acidified with IN aqueous citric acid and extracted with EtOAc. The organics were dried (MgSO4) and concentrated in vacuo to yield after recrystallization compound X5 (220mg): 1H-NMR (CDCl3, 500MHz) 3.63 (s, 1 H), 2.45 (s, 2H), 1.22- 1.64 (m, 1 OH) ppm; FIA m/z 157.2 ES".
With iodine; zinc; In tetrahydrofuran; for 5h;Heating / reflux;
Reference Example 61; (1-Hydroxycyclohexyl) ethyl acetate; To a solution of cyclohexanone (9.52 g, 97.0 mmol), a zinc powder (7.6 g, 116.4 mmol) and a small amount of iodine in THF (100 ml) was added dropwise ethyl bromoacetate (11.8 ml, 106.7 mmol) under a nitrogen atmosphere, and the mixture was heated under reflux for 5 hrs. 10% Sulfuric acid (100 ml) was carefully added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous MgS04, and concentrated under reduced pressure to give the title compound (17.2 g, 94%) as a colorless oil. ¹H-NMR (CDCl3) No.: 1 . 27 (3H, t, J=7.0 Hz) , 1.35-1.71 (10H, m), 2.46 (2H, s), 3.43 (lH, s), 4.17 (2H, q, J=7.4 Hz).
[00302] Compound X4 was prepared using essentially the procedure described in Bull.Chem. Soc. Jpn., 1971, 44, 1090. Specifically, A solution of ethylbromoacetate (8.3 mL) (Aldrich Chemical Co., Milwaukee, Wisconsin, USA) in toluene was added dropewise at 8O0C over 30 min. to a thoroughly stirred mixture of cyclohexanone X3 (4.9 g) and zinc powder (4.9 g) in toluene. The addition was carefully monitored and the temperature was kept at 800C. After the addition was completed, the mixture was refluxed for 90 min., cooled, decomposed with IN aqueous HCl, and extracted with Et2O. The organics were washed with EPO <DP n="302"/>water, aq. NaHCO3, dried (MgSO4) and concentrated in vacuo to yield X4 (5.9g): 1H-NMR(CDCl3, 500MHz) 4.16 (t, 2H), 3.0 (br s, IH), 2.46 (s, 2H), 1.40-1.69 (m, 10H), 1.27 (t, 3H) ppm; FIA m/z 187.1 ES+.
[0337] Compound X4 was prepared using essentially the procedure described in Bull.Chem. Soc. Jpn., 1971, 44, 1090. Specifically, A solution of ethylbromoacetate (8.3 mL) (Aldrich Chemical Co., Milwaukee, Wisconsin, USA) in toluene was added dropewise at 8O0C over 30 min. to a thoroughly stirred mixture of cyclohexanone X3 (4.9 g) and zinc powder (4.9 g) in toluene. The addition was carefully monitored and the temperature was kept at 80 0C. After the addition was completed, the mixture was refiuxed for 90 min., cooled, decomposed with IN aqueous HCl, and extracted with Et2O. The organics were washed with water, aq. NaHCO3, dried (MgSO4) and concentrated in vacuo to yield X4 (5.9g). 1H-NMR (CDCl3, 500MHz) 4.16 (t, 2H), 3.0-(br s, IH), 2.46 (s, 2H), 1.40-1.69 (m, 10H), 1.27 (t, 3H) ppm; FIA m/z 187.1 ES+.
Under nitrogen atmosphere, 30 ML of THF was added to 6.09 g (10 mmol, 1.0 equivalent) of (BrZnCH2COOEt·THF)2.. Under argon atmosphere, a solution of 0.98 g (10 mmol) of cyclohexanone in 5 ML of THF was added dropwise while stirring at 0?5C. The mixture was stirred at 20?25C for 3 hours. 15 ML of 1N hydrochloric acid was added dropwise at 20C or lower, followed by dilution with 50 ML of ethyl acetate.. Then, the layers were separated.. The organic layer was washed successively with 10 ML (*2) of 1N hydrochloric acid, 10 ML of an aqueous saturated sodium chloride solution, 20 ML (*2) of an aqueous saturated sodium bicarbonate solution, and 10 ML (*2) of an aqueous saturated sodium chloride solution.. After washing, the organic layer was dried with anhydrous magnesium sulfate.. Concentration under reduced pressure afforded 1.76 g of the desired product (yield 95%).1H NMR (CDCl3), (ppm): delta 1.28 (3H, t, J=7.1 Hz), 1.38-1.74 (10H, m), 2.46 (2H, s), 3.40 (1H, s), 4.17 (2H, q,J=7.1Hz).
ethyl 1-hydroxy-4-[4-(2-aminoethyl)-1-piperazinyl]cyclohexaneacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Preparation F Preparation of Ethyl 1-hydroxy-4-[4-(2-aminoethyl)-1-piperazinyl]cyclohexaneacetate Following the procedure of Preparation E, except substituting ethyl 1-(hydroxy)cyclohexaneacetate for ethyl 4-oxo-1-piperidineacetate, gives the title compound.
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