Category: 627-32-7

627-32-7,Some common heterocyclic compound, 627-32-7, name is 3-Iodo-1-propanol, molecular formula is C3H7IO, 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.

Cesium carbonate [(5.] 54 g) is added to a solution [OFN (4-CHLOROBENZYL)-4-HYDROXY 2-] (hydroxymethyl) thieno [2, [3-B]] [PYRIDINE-5-CARBOXAMIDE] (5.23 g, prepared as described in US 6,239, 142) and 2-(3-iodopropoxy)tetrahydro-2H-pyran (4.32 g, prepared by mixing equal molar amounts of 2-iodopropanol and 3, 4-dihydro-2H-pyran) in DMF (20 mL). The mixture is heated at [60 C] for 4 hours. The solvent is evaporated and the residue is dissolved in 10% [MEOH] in [CH2C12.] The mixture is washed with water and the organic layer is dried (MgSO4), filtered, and concentrated. The crude product is purified by column chromatography [(CH2CLJMETHANOL,] [95/5)] followed by recrystallization from EtOAc to afford 4.82 g of the title compound as white crystals. Physical characteristics. 1H NMR (400 [MHZ,] DMSO-d6) 8 10.55, 8.71, 7.39, 7.33, 7.29, 5.79, 4. [70,] 4.53, 4.49, 4. [38, 3.] 68,3. [37,] 2.11, 1.63, 1.53, 1.40 ; MS [(EI)] m/z 490 [(MF)] ; Anal. Found: C, 58.74 ; H, 5.66 ; N, 5.61.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-1-propanol, its application will become more common.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; FLECK, Bruce, Francis; WO2004/22567; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 627-32-7, name is 3-Iodo-1-propanol, I believe this compound will play a more active role in future production and life. 627-32-7

Example 31 Synthesis of OS-1-CA Conjugate 48 (FIG. 24) Compound 46 To a solution of oseltamivir carboxylic acid N-Boc derivative (64, 60 mg, 0.16 mmol) in MeOH (0.5 mL) was added KOH (6.87 mg, 0.17 mmol). The mixture was stirred at room temperature for 30 min, and then concentrated under reduced pressure. The residue was dissolved in DMF (0.5 mL), and then added 3-iodo-1-propanol (17 mL, 0.19 mmol). After stirring at 50 C. for 4 h, the mixture was evaporated under reduced pressure. The residues was dissolved in CH2Cl2 (10 mL) and extracted with 1 M HCl and brine, dried over MgSO4, concentrated under reduced pressure, and purified by flash silica gel column chromatography (EtOAc/hexane, 2:1) to afford compound 65 (50 mg, 72%). C22H38N2O7; white solid; mp 93-95 C.; TLC (EtOAc/n-hexane, 2:1) Rf=0.31; [alpha]D22=-81.9 (c=1.0, CH2Cl2); IR (film) 3309, 2964, 2935, 2878, 1686, 1536, 1458, 1392, 1368, 1295, 1255, 1172, 1057 cm; 1H NMR (400 MHz, CDCl3) delta 6.77 (1H, s), 5.88 (1H, d, J=8.8 Hz), 5.11 (1H, d, J=9.6 Hz), 4.28-4.31 (2H, m), 4.01-4.08 (1H, m), 3.95 (1H, d, J=7.2 Hz), 3.73-3.82 (1H, m), 3.70 (2H, t, J=6.0 Hz), 3.30-3.34 (1H, m), 2.72 (1H, dd, J=17.6, 5.2 Hz), 2.26 (1H, dd, J=18.0, 10.0 Hz), 1.97 (3H, s), 1.87-1.93 (2H, m), 1.47-1.57 (4H, m), 1.41 (9H, s), 0.85-0.91 (6H, m); 13C NMR (100 MHz, CDCl3) delta 170.9, 165.9, 156.2, 138.1, 128.8, 82.3, 79.5, 75.8, 61.8, 58.6, 54.6, 49.3, 31.5, 30.9, 28.4 (3*), 26.2, 25.7, 23.3, 9.7, 9.3; HRMS calcd for C22H39N2O7: 443.2757, found: m/z 443.2753 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 627-32-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Academia Sinica; Wong, Chi-Huey; Fang, Jim-Min; Liu, Kung-Cheng; Jan, Jia-Tsrong; Cheng, Yih-Shyun E.; Cheng, Ting-Jen R.; US2013/274229; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

627-32-7, Name is 3-Iodo-1-propanol, 627-32-7, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

General procedure: 4.2.1.7 10-(3-Hydroxypropoxy)-3,9-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-2-ol (16) Yield 76%; reddish-brown solid, mp 73-78 C; 1H NMR (CDCl3, 500 MHz) 6.87-6.80 (m, 3H), 6.60 (s, 1H), 4.22 (d, J = 15.7 Hz, 1H), 4.16 (td, J = 6.1, 1.5 Hz, 2H), 3.91-3.84 (m, 8H), 3.52 (d, J = 15.4 Hz, 2H), 3.27-3.10 (m, 3H), 2.80 (dd, J = 15.7, 11.6 Hz, 1H), 2.68-2.61 (m, 2H), 2.07 (quint, J = 5.8 Hz, 2H); 13C NMR (CDCl3, 125 MHz) delta 149.4, 145.4, 145.1, 143.9, 130.5, 128.8, 128.4, 126.1, 124.1, 112.5, 111.3, 110.6, 67.5, 61.0, 60.3, 59.2, 55.9, 54.0, 51.6, 36.3, 32.1, 29.2; HRMS (ESI) m/z calcd for C22H27NO5 [M+H]+, 386.1884, found 386.1897.

Statistics shows that 3-Iodo-1-propanol is playing an increasingly important role. we look forward to future research findings about 627-32-7.

Reference:
Article; Gadhiya, Satishkumar; Madapa, Sudharshan; Kurtzman, Thomas; Alberts, Ian L.; Ramsey, Steven; Pillarsetty, Nagavara-Kishore; Kalidindi, Teja; Harding, Wayne W.; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 2060 – 2071;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com