Electric Literature of 17366-48-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 17366-48-2 as follows.
1-(Diphenylmethyl)azetidin-3-one (see Bioorg. Med. Chem. Lett.; 13; 2003; 2191-2194, 2.12 g, 9.0 mmol) was dissolved in methylene chloride (25 mL) and the resultant solution was added to a slurry of exo-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (norpseudotropine hydrochloride) (see U.S. Pat. No. 6,699,870, 2.12 g, 9.0 mmol) in methylene chloride (25 mL). Another portion of methylene chloride (20 mL) was added and then DIPEA (3.47 g, 26.8 mmol), acetic acid (1.09 g, 18.2 mmol) and sodium triacetoxyborohydride (3.79 g, 17.9 mmol) were added in the given order. The mixture was stirred at RT for 4 days and then diluted with methylene chloride (150 mL). The solution was washed with a mixture of aqueous Na2CO3 (sat. 20 mL) and aqueous NaHCO3 (sat. 15 mL) and then washed with aqueous NaHCO3 (sat. 15 mL). The organic solution was dried (Na2SO4) and then the solvent was removed by evaporation. The product was purified twice by column chromatography on silica gel first eluting with methylene chloride/methanol (95/5) and then with methylene chloride/ammonia saturated methanol (9/1). There was obtained 1.9 g (60%) of exo-8-[1-(diphenylmethyl)azetidin-3-yl]-8-azabicyclo[3.2.1]octan-3-ol as a white foam. 1H NMR (400 MHz, CDCl3). 1.4-1.6 (m, 4H), 1.7-2.0 (m, 4H), 2.8-2.9 (b, 2H), 3.1 (b, 2H), 3.3-3.5 (m, 3H), 3.8-3.9 (m, 1H), 4.4-4.5 (s, 1H), 7.2 (m, 2H), 7.3 (m, 4H), 7.4 (m, 4H); LCMS: m/z 349 (M+1)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17366-48-2, its application will become more common.
Reference:
Patent; Antonsson, Thomas; US2008/146538; (2008); A1;,
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