Aminocyclohexyl ether compounds and uses thereof
a technology of cyclohexyl ether and compounds, which is applied in the direction of biocide, drug compositions, cardiovascular disorders, etc., can solve the problems that antiarrhythmic compounds may actually increase mortality in patients who have had a myocardial infarction, and no satisfactory pharmacotherapy for the treatment and/or prevention of ventricular fibrillation during acute,
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example 1
(1R,2R)-2-[(3R)-Hydroxypyrrolidinyl]-1-(3,4-dimethoxyphenethoxy)cyclohexane monohydrochloride (Compound 1)
The reaction scheme for the preparation of compound 1 described herein is illustrated in FIG. 1.
[0888] Preparation of Intermediates
N-tert-Butoxycarbonyl-3R-pyrrolidinol (1R)
[0889] To a cold (0° C.) stirred solution of (R)-3-pyrrolidinol (20.6 g, 236 mmol; Omega cat. # HP-2113) in anhydrous THF (800 mL) was added dropwise a solution of di-tert-butyldicarbonate (56.7 g, 260 mmol, Aldrich cat. # 20,524-9) in THF (200 mL), and the resultant solution was stirred at room temperature for 18 h. Concentration in vacuo of the reaction mixture and short-path distillation in vacuo of the clear yellow residue gave 1R (42 g, 95% yield) as clear and colourless oil, which crystallized on standing.
[0890] Characterization: Rf 0.58 (CHCl3-MeOH, 4:1, v / v), 1H NMR (200 MHz, CDCl3) δ 4.4 (br s, 1H), 3.5-3.2 (m, 4H), 2.5 (br s, 1H), 2.0-1.9 (m, 2H), 1.4 (s, 9H); 13C NMR (75 MHz, CDCl3) δ 154.7, ...
example 2
(1S,2S)-2-[(3R)-Hydroxypyrrolidinyl]-1-(3,4-dimethoxyphenethoxy)cyclohexane monohydrochloride (Compound 2)
[0947] 5SSR, (1S,2S)-2-[(3R)-benzyloxypyrrolidinyl]-1-(3,4-dimethoxyphenethoxy)cyclohexane was prepared and resolved according to Example 1. Compound 2 was then obtained from 5SSR using the procedure described above in example 1 with respect to the preparation of Compound 1.
[0948] Characterization: Calcd for C20H31NO4.HCl: C, 62.24; H, 8.36; N, 3.63. Found: C, 62.20; H, 8.46; N, 3.55. [α]D+26.690 (c 13.04 g / L, CHCl3)
example 3
(1R,2R) / (1S,2S)-2-[(3R) / (3S)-Hydroxypyrrolidinyl]-1-(3,4-dimethoxyphenethoxy)-cyclohexane monohydrochloride (Compound 3)
Preparation of Intermediates
[0949] N-Benzyloxycarbonyl-3-pyrrolidinol (1b). To a cold (−60° C.) solution of 1a (20.0 g, 225 mmol) and Et3N (79 mL, 560 mmol) in CH2Cl2 (200 mL) was added dropwise a solution of benzyl chloroformate (34 mL, 225 mmol) in CH2Cl2 (80 mL). After the addition was completed within 45 min, the reaction mixture (a yellow suspension) was allowed to warm up to room temperature and was stirred under argon at room temperature overnight. The reaction mixture was then quenched with 1M HCl aq (350 mL) and the organic layer was collected. The acidic aqueous layer was extracted with CH2Cl2 (2×150 mL) and the combined organic layers were dried. Evaporation in vacuo of the solvent provided 59.6 g of pale yellow oil, which was further pumped under high vacuum for 15 min to yield 58.2 g (17% over theoretical yield) of 1b suitable for the next step witho...
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