Analyzing the synthesis route of 2-(Aziridin-1-yl)ethanol

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1072-52-2, 2-(Aziridin-1-yl)ethanol, and friends who are interested can also refer to it.

Reference of 1072-52-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1072-52-2, name is 2-(Aziridin-1-yl)ethanol. A new synthetic method of this compound is introduced below.

Example 10 (Table 1, entry 4 and Scheme 7): Preparation of 2- [(2-iodoethyl)-2,4- dinitro-6-({[2-(tetrahydro-2/£pyran-2-yloxy)ethyl]amino}carbonyl)anih’no]ethyl methanesulfonate (17c); A slurry of 15 (520 mg, 1.4 mmol) in dry 3-methyl-2-butanone (20 mL) and NaI (3.1 g) was cooled to below 5 0C, and aziridineethanol (240 mg, 2.76 mmol) was added. The reaction was kept at 20 0C overnight, then water (100 mL) was added, and the mixture was extracted with EtOAc (3×50 mL). The combined organic layer was washed with water, dried and concentrated under pressure, then passed through a short column of silica gel, eluting with heptane/EtOAc (1:1), to give 2-[(2-hydroxyethyl)(2-iodoethyl)amino]-3,5- dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (16c) (630 mg, 82%) as a yellow foam; 1H NMR (CDCl3) delta 8.63 (d, / = 2.8 Hz, 1 H), 8.56 (dj = 2.8 Hz, 1 H), 8.24 (br, 1 H), 4.54 (m, 1 H), 4.48 (m, 1 H), 3.93 (m, 2 H), 3.84 (m, 1 H), 3.70 (m, 6 H), 3.54 (m, 1 H), 3.30 (m, 2 H), 3.18 (m, 2 H), 1.90-1.40 (m, 6 H); 13C NMR delta 165.7, 146.7, 144.4, 140,9, 134.5, 129.2, 123.5, 101.6, 67.0, 65.4, 58.0, 55.0, 53.7, 40.7, 31.3, 25.1, 21.2, 0.3; HRMS (FAB) calcd for C18H26IN4O8 [MH]+ m/z 553.0795; found 533.0797.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1072-52-2, 2-(Aziridin-1-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2008/30112; (2008); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts