tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylate

Uses

tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylate is a useful intermediate for organic synthesis.

Synthesis

The general procedure for the synthesis of 4-oxime-1-Boc-piperidine using N-Boc-4-piperidone as starting material is as follows: 1 equiv. of N-Boc-4-piperidone, 1.6 equiv. of hydroxylamine hydrochloride, and 2.0 equiv. of sodium acetate were dissolved in an aqueous methanol solution, mixed homogeneously, and then heated to reflux the reaction. Upon completion of the reaction, the target product 4-oxime-1-Boc-piperidine was obtained in quantitative yield. The synthetic method was applicable for the preparation of all oxime substrates in this study.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2942 - 2945
[2] Tetrahedron Letters, 2010, vol. 51, # 24, p. 3216 - 3217
[3] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
[4] Patent: EP1477490, 2004, A1. Location in patent: Page 109
[5] Patent: WO2008/150447, 2008, A1. Location in patent: Page/Page column 206