Reagent for Preparation of Weinreb Amides

No.153(December 2014)

M2117: N-Methoxy-N-methylcarbamoyl Chloride (1)

N-Methoxy-N-methylamides (Weinreb amides) are well known as precursors to site-selective synthesis of unsymmetrical ketones.

In recent years, various synthetic methods for Weinreb amides using N-methoxy-N-methylcarbamoyl chloride (1) have been reported. According to their reports, Weinreb amides are synthesized by the reaction of 1 with organoboronic acids,¹⁾ organostannanes,²⁾ Grignard reagents³⁾ and alkylphosphonates,⁴⁾ respectively.

References

1)Palladium-catalyzed preparation of Weinreb amides from boronic acids and N-methyl-N-methoxycarbamoyl chloride
- R. Krishnamoorthy, S. Q. Lam, C. M. Manley, R. J. Herr, J. Org. Chem. 2010, 75, 1251.
2)Palladium-catalyzed coupling reactions of N-methoxy-N-methylcarbamoyl chloride for the synthesis of N-methoxy-N-methylamides
- M. Murakami, Y. Hoshino, H. Ito, Y. Ito, Chem. Lett. 1998, 27, 163.
3)A novel synthesis of N-methoxy-N-methylamides from 4,6-pyrimidyl urethane and Grignard reagents
- J. I. Lee, Bull. Korean Chem. Soc. 2007, 28, 695.
4)Preparation of [1-(methoxymethylcarbamoyl)ethyl]phosphonic acid bis-(2,2,2-trifluoroethyl)ester: A useful intermediate in the synthesis of Z-unsaturated N-methoxy-N-methylamides
- A. B. Smith, III, J. J. Beiger, A. H. Davulcu, J. M. Cox, Org. Synth. 2005, 82, 147.

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Reagent for Preparation of Weinreb Amides

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