Category: 180976-09-4

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. 180976-09-4, name is tert-Butyl (cyanomethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below., SDS of cas: 180976-09-4

Preparation of tert-butyl (1-cyano-2-(4-fluorophenyl)ethyl)(methyl)carbamate 1-9 [0119] A mixture of tert-butyl (cyanomethyl)(methyl)carbamate (500 mg, 2.94 mmol) in THF (3 mL) was stirred at -78 oC under N2. LDA (2.203 ml, 4.41 mmol) and DMPU (1.417 ml, 11.75 mmol) were added dropwise at -78 oC. The reaction mixture was stirred at this temperature for 1 h. 1-8 (833 mg, 4.41 mmol) was added dropwise at -78 oC. The mixture was stirred at -78 oC for 1 h. The mixture was diluted with EtOAc (100 mL), washed with aq. NH4Cl (100 mL), dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by prep-TLC (PE: EA = 10:1) to give 1-9. [0120] 1H NMR (CDCl3, 400 MHz) delta 7.177.02 (m, 2H), 7.006.98 (m, 2H), 5.355.02 (m, 1H), 3.112.90 (m, 5H), 1.561.42 (m, 9H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ROECKER, Anthony, J.; LAYTON, Mark, E.; GRESHOCK, Thomas, J.; PERO, Joseph, E.; KELLY, Michael, J., III; ZHANG, Ting; (75 pag.)WO2017/165204; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 180976-09-4,Some common heterocyclic compound, 180976-09-4, name is tert-Butyl (cyanomethyl)(methyl)carbamate, molecular formula is C8H14N2O2, 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.

A solution of cyanomethyl-methyl-carbamic acid tert-butyl ester (6.01 g, 35.3 mmol) and hydroxylamine (5.13 g, 77.6 mmol, 50percent solution in water) in ethanol (30 mL) was heated at reflux for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was azeotroped twice with ethanol, then once with isopropyl alcohol to afford a white solid. This was triturated with ether and collected by filtration, then dried under vacuum at room temperature to afford the title compound (5.27 g) as a white solid. A further crop could be obtained from the mother liquors by the same work-up procedure. Total yield 6.93 g (96percent). 1H NMR (CDCI3): 1.48 (S, 9 H), 2.87 (s, 3 H), 3.84 (s, 2 H), 4.73 (brs., 1 H), 5.09 (bra., 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (cyanomethyl)(methyl)carbamate, its application will become more common.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB; WO2008/23157; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts