With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.223734-62-1,2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
Example 1. Preparation of chiral benzyl alcohol (A-l); A 50-mL, two-necked, round-bottom flask equipped with a mechanical stirrer was charged with zinc triflate (2.16g, 0.0059 mol) and (+)-N-methylephiderine (0.814 g, 0.0045 mol) in toluene (10 mL). To this mixture triethyl amine was added (0.459 g, 0.0045 mol) and this gelatinous mixture was stirred at ambient temperature for 30-60 minutes. To this mixture was then treated with a solution of alkyne (1.08 g, 0.0045 mol) in toluene (1 mL), stirred at ambient temperature for 15 minutes followed by solution of aldehyde (0.250 g, 0.0014 mol). Progress of the reaction was monitored by TLC (completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 20% ethyl acetate in hexanes). After stirring the mixture for 3 h TLC indicated completion of reaction. At this stage reaction mixture was quenched by slow addition of saturated ammonium chloride (10 mL). This was stirred for 5-10 minutes and organic layer containing desired compound was separated. Aqueous layer was washed with ethyl acetate (10 mL). The combined organic layers were washed with brine (15 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain a crude product (2.0 g). The crude product was purified by column chromatography using 250- 400 mesh silica gel. A solvent gradient of ethyl acetate in hexanes (5-20%) was used to elute the product from the column. All fractions containing the desired product were combined and concentrated in vacuo to give pure chiral benzyl alcohol A-l (0.360g, -87%) compound was characterized by .H, 13C NMR, IR, LCMS and chiral HPLC data. 1H NMR (CDC13, 300 MHz): delta 0.87 (t, 3H), 1.18-1.86 (m, 17H), 2.28 (dt, 1H), 2.34-2.45 (m, 2H), 3.40- 3.53 (m, 1H), 3.54- 3.62 (m, 1H), 3.63-3.75 (m, 1H), 3.81 (s, 3H, OCH3), 3.83-3.92 (m, 1H), 4.62-4.66 (m, 1H), 4.89-5.05 (m, 2H), 5.59-5.61 (merged two s, 1H), 5.91-6.04 (m, 1H), 6.85-6.82 (d, 1H), 7.20- 7.26 (m, 1H), and 7.31-7.36 (m, 1H); 13C NMR (CDC13, 75 MHz): delta 14.13, 14.18, 14.98, 15.56, 19.96, 21.14, 22.71, 24.77, 25.34, 25.57, 29.51, 31.17, 31.23, 32.07, 32.19, 32.69, 33.51, 33.94, 35.13, 55.86, 60.49, 62.12, 62.18, 62.82, 75.36, 75.89, 80.20, 80.53, 86.97, 87.42, 97.31, 98.06, 1 10.63, 1 14.80, 1 19.18, 1 19.27, 125.86, 127.44, 127.50, 137.15, 140.78, 157.68; IR: 341 1 , 2230, 1638, 1259, 1 133, 1023, 755 cm”1; MS( /z): [M+Na]+ 437.35.
223734-62-1, 223734-62-1 2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran 11149121, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; UNITED THERAPEUTICS CORPORATION; BATRA, Hitesh; PENMASTA, Raju; SHARMA, Vijay; TULADHAR, Sudersan M.; WALSH, David A.; WO2011/153363; (2011); A1;,
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