ChemicalBook CAS DataBase List 2-(N-BOC-METHYLAMINO)ACETONITRILE

2-(N-BOC-METHYLAMINO)ACETONITRILE synthesis

5synthesis methods

Product Name:2-(N-BOC-METHYLAMINO)ACETONITRILE
CAS Number:180976-09-4
Molecular formula:C8H14N2O2
Molecular Weight:170.21

24424-99-5

25808-30-4

180976-09-4

GENERAL STEPS: To a dichloromethane (DCM, 100 mL) suspension of 2-methylaminoacetonitrile hydrochloride (11.45 g, 107.4 mmol) was added triethylamine (31.5 mL, 226 mmol), followed by the slow addition of di-tert-butyl dicarbonate (22.3 g, 102.2 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was filtered to remove insoluble salts and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a 10-20% ethyl acetate/cyclohexane gradient elution. Fractions containing the target product were collected, combined and concentrated under reduced pressure to give tert-butyl (cyanomethyl)(methyl)carbamate (11.94 g, 69% yield) as a colorless liquid.LC-MS (Method 5): retention time 2.82 min, [M + H]+ m/z 171.1.

24424-99-5 Synthesis

24424-99-5
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25808-30-4
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180976-09-4
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Yield:180976-09-4 100%

Reaction Conditions:

with sodium carbonate in methanol;water; for 2.5 h;Ambient temperature;

References:

Li, Qun;Chu, Daniel T. W.;Claiborne, Akiyo;Cooper, Curt S.;Lee, Cheuk M.;Raye, Kathleen;Berst, Kristine B.;Donner, Pamela;Wang, Weibo;Hasvold, Lisa;Fung, Anthony;Ma, Zhenkun;Tufano, Michael;Flamm, Robert;Shen, Linus L.;Baranowski, John;Nilius, Angela;Alder, Jeff;Meulbroek, Jonathan;Marsh, Kennan;Crowell, DeAnne;Hui, Yuhua;Seif, Louis;Melcher, Laura M.;Henry, Rodger;Spanton, Steven;Faghih, Ramin;Klein, Larry L.;Tanaka, S. Ken;Plattner, Jacob J. [Journal of Medicinal Chemistry,1996,vol. 39,# 16,p. 3070 - 3088]