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Aminolysis of methyl isocyanoacetate with pyrrolidine; 2-Isocyano-1-(pyrrolidin-1-yl)ethanone

SyntheticPage 833
DOI: 10.1039/SP833
Submitted Feb 09, 2018, published Feb 12, 2018
Stephen Habay (sahabay@salisbury.edu), Abhishek Purohit (apurohit1@gulls.salisbury.edu)


			Reaction Scheme: <IMG src="/images/empty.gif"><IMG src="/images/empty.gif"><IMG src="/images/empty.gif">Aminolysis of <SPAN id=csm1518537426736 class=csm-chemical-name title="methyl isocyanoacetate" grpid="1">methyl isocyanoacetate</SPAN> with <SPAN id=csm1518537934383 class=csm-chemical-name title=pyrrolidine grpid="2">pyrrolidine</SPAN><IMG src="/images/empty.gif"><IMG src="/images/empty.gif"><IMG src="/images/empty.gif">

Chemicals Used

Methyl isocyanoacetate (95 %, Acros)
Pyrrolidine (99 %, Sigma-Aldrich)

Procedure

To a flask of magnetically stirred pyrrolidine (4.19 mL, 51.2 mmol) was added dropwise methyl isocyanoacetate (4.9 mL, 51.2 mmol). The reaction was stirred at room temperature for 20 min or until the solution solidified. The solid residue was dissolved in ethyl acetate (100 mL) and vacuum filtered through a 1 inch deep plug of silica gel. The silica plug was washed with two additional portions of ethyl acetate (50 mL). The combined filtrate was concentrated by rotary evaporation, leaving a tan solid product (6.58 g, 93 %), which was dried under vacuum . 

Author's Comments

On larger scales, the reaction flask is immersed in an ambient temperature water bath during the addition of methyl isocyanoacetate to prevent a large temperature change.

The color of the product can vary from light yellow to orange-brown.

Data

mp = 69-72 °C
IR (ATR): 2978, 2162, 1653, 1448, 1415, 1329 cm-1
1
H-NMR (400 MHz, CDCl3): δ ppm 4.22 (s, 2 H) 3.50 (t, J = 6.9 Hz, 2 H) 3.38 (t, J = 6.8 Hz, 2 H) 1.94 - 2.05 (m, 2 H) 1.83 - 1.93 (m, 2 H)
13C-NMR (100 MHz, CDCl3): δ ppm 160.52, 160.23, 46.49, 46.09, 44.91, 26.01, 23.93

Lead Reference

Dömling, A; Beck, B.; Fuchs, T.; Yazbak, A. J. Comb. Chem., 2006, 8, 872–880.

Other References

Mossetti, R.; Caprioglio, D.; Colombano, G.; Tron, G.C.; Pirali, T. Org. Biomol. Chem., 2011, 9, 1627-1631.

Supplementary Information

e.g. Actual NMR spectra (as images or jdx files for interactive spectra), photographs of apparatus, TLC’s or crystals or videos. Please contact the ChemSpider team (ChemSpider-at-rsc.org) for help with this.
IR spectrum (Product IR.pdf)
1H NMR (1H NMR.pdf)
13C NMR (13C NMR.pdf)

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Get structure file (.cdx, .sk2, .mol)

Keywords: amides, esters, isocyanide, isonitrile, nucleophilic, substitution

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