As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 627-32-7 name is 3-Iodo-1-propanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 627-32-7
Mitragynine (50.0 mg, 0.126 mmol) was dissolved in 3-iodopropanol (0.33 mL), and acetonitrile (CH3CN, 0.5 mL) was added to the solution. Under ice cooling, IBDA (40.5 mg, 0.126 mmol) was added in four portions at intervals of 4 minutes, and the mixture was stirred at room temperature for 1 hour in an argon atmosphere. The reaction liquid was poured into an ice-cold saturated sodium bicarbonate aqueous solution and extracted three times with ether. The extracted organic layers were washed with brine and dried over sodium sulfate, followed by evaporation of the solvent under reduced pressure and vacuum drying. Thus, a residue was obtained. The resultant residue was purified by medium pressure liquid chromatography (aminosilica gel, 30% ethyl acetate/n-hexane) to obtain an iodinated form represented by the following formula (V) (31.9 mg, 46% yield).Analysis data of the product are shown below. 1H-NMR (400 MHz, CDCl3) delta [ppm]: 7.45 (1H, s, H-17), 7.32 (1H, dd, J=8.0, 8.0 Hz, H-11), 7.24 (1H, d, J=7.6 Hz, H-12), 6.75 (1H, d, J=8.1 Hz, H-10), 3.87 (3H, s, 9-OCH3), 3.81 (3H, s, 17-OCH3), 3.71 (3H, s, 22-OCH3), 3.29 (2H, m, H2-1?), 3.05-2.98 (3H, overlapped, H-3, H-5, and H-15), 2.93 (2H, dd, J=5.3, 5.3 Hz, H2-3?), 2.89-2.70 (3H, overlapped, H-6, H-14, and H-21), 2.59 (1H, m, H-5), 2.45 (1H, dd, J=11.2, 2.6 Hz, H-21), 2.08-1.88 (3H, overlapped, H-14 and H2-2?), 1.74-1.56 (3H, overlapped, H-6, H-19, and H-20), 1.23 (1H, m, H-19), 0.82 (3H, dd, J=7.2, 7.2 Hz, H3-18).13C-NMR (100 MHz, CDCl3) delta [ppm]: 184.0 (C-2), 169.3 (C-22), 160.7 (C-17), 156.5 (C-9), 155.5 (C-13), 130.9 (C-11), 123.0 (C-8), 114.3 (C-12), 111.2 (C-16), 108.8 (C-10), 86.1 (C-7), 63.2 (C-1?), 62.2 (17-OCH3), 61.8 (C-3), 58.1 (C-21), 55.4 (9-OCH3), 51.3 (22-OCH3), 50.3 (C-5), 40.5 (C-20), 39.3 (C-15), 35.2 (C-6), 33.7 (C-2?), 25.9 (C-14), 18.9 (C-19), 12.8 (C-18), 3.7 (C-3?).UV (MeOH) lambdamax: 301.0, 245.5 (sh), 221.5 nm.CD (0.151 mM, MeOH, 24 C.), lambda nm (De): 345 (0), 309 (+2.8), 290 (0), 281 (-0.8), 275 (0), 258 (+4.8), 242 (0), 221 (-9.4), 210 (0). EI-MS (%) m/z: 582 (M+, 41), 397 (100).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-propanol, and friends who are interested can also refer to it.
Reference:
Patent; NATIONAL UNIVERSITY CORPORATION CHIBA UNIVERSITY; TAKAYAMA, Hiromitsu; (11 pag.)US2016/340352; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com