These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,624-95-3, its application will become more common.
Electric Literature of 624-95-3 ,Some common heterocyclic compound, 624-95-3, molecular formula is C6H14O, 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.
Dimethylsulfoxide (6.80 mL, 95.7 mmol) was added over 5 min to a solution of oxalylchloride (23.9 mL, 47.8 mmol) in dichloromethane at -78 0C. The resulting mixture was stirred at -78 0C for 5 min, then 3,3-dimethyl-butan-l-ol (5.22 mL, 43.1 mmol) was added. After stirring an additional 30 min at -78 0C, triethylamine (23.3 mL, 167 mmol) was added and the reaction mixture warmed to 0 0C and stirred at that temperature for 45 min. The mixture was then transferred to a separatory funnel and was washed with 0.5 M aqueous hydrochloric acid. The organic layer was dried over sodium sulfate, filtered and was concentrated in vacuo to a volume of about 70 mL (water bath temperature = 0 0C). Methanol (100 mL) was added followed sequentially by 1 -amino- lH-pyrrole-2-carboxylic acid allyl ester (Example Ib, 7.16 g, 43.1 mmol), acetic acid (6 mL), and sodium cyanoborohydride (5.42 g, 86.3 mmol). The reaction mixture was stirred at 23 0C for 2 h, and then was partitioned between saturated aqueous sodium bicarbonate solution (400 mL) and a 1 : 1 mixture of ethyl acetate and hexanes (2 x 200 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (Merck silica gel 60, 40-63 mum, 5?10% ethyl acetate in hexanes) afforded the desired product, l-(3,3-dimethyl-butylamino)-lH-pyrrole-2- carboxylic acid allyl ester (4.04 g, 16.15 mmol, 37% yield) as a clear liquid. 1H NMR (400 MHz, CDCl3) delta: 0.91 (9H, s), 1.42 – 1.46 (2H, m), 2.98 – 3.04 (2H, m), 4.75 – 4.77 (2H, m), 5.26 – 5.28 (IH, m), 5.37 – 5.41 (IH, m), 5.96 – 5.99 (IH, m), 6.01 – 6.05 (IH, m), 6.27 – 6.30 (IH, m), 6.89 – 6.91 (IH, m), 6.96 – 6.98 (IH, m).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,624-95-3, its application will become more common.
Reference:
Patent; ANADYS PHARMACEUTICALS, INC.; WO2007/150001; (2007); A1;,
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