A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles

Moshkin, Vladimir Sergeevich; Sosnovskikh, Vyacheslav Yakovlevich

doi:10.1016/j.mencom.2015.11.014

Home / Publications / A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles

A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles

Vladimir Sergeevich Moshkin ¹

Vladimir Sergeevich Moshkin

0000-0001-7673-1852

,

Vyacheslav Yakovlevich Sosnovskikh ¹

Vyacheslav Yakovlevich Sosnovskikh

0000-0002-8956-0973

¹ Department of Chemistry, Ural Federal University, Ekaterinburg, Russian Federation

10.1016/j.mencom.2015.11.014

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Published 2015-11-09

Communication , Volume 25, Issue 6, 440-442

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Moshkin V. S., Sosnovskikh V. Y. A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 440-442.

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Moshkin V. S., Sosnovskikh V. Y. A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 440-442.

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TY - JOUR

DO - 10.1016/j.mencom.2015.11.014

UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.014

TI - A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles

T2 - Mendeleev Communications

AU - Moshkin, Vladimir Sergeevich

AU - Sosnovskikh, Vyacheslav Yakovlevich

PY - 2015

DA - 2015/11/09

PB - Mendeleev Communications

SP - 440-442

IS - 6

VL - 25

ER -

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@article{2015_Moshkin,

author = {Vladimir Sergeevich Moshkin and Vyacheslav Yakovlevich Sosnovskikh},

title = {A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles},

journal = {Mendeleev Communications},

year = {2015},

volume = {25},

publisher = {Mendeleev Communications},

month = {Nov},

url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.014},

number = {6},

pages = {440--442},

doi = {10.1016/j.mencom.2015.11.014}

}

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Moshkin, Vladimir Sergeevich, and Vyacheslav Yakovlevich Sosnovskikh. “A novel synthesis of 2-alkyl(aryl)pyrrolidines from proline via 2,3-diphenylhexahydropyrrolo[2,1-b]oxazoles.” Mendeleev Communications, vol. 25, no. 6, Nov. 2015, pp. 440-442. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.014.

Abstract

Diphenyloxapyrrolizidines, products of the reaction between proline and benzaldehyde, are convenient building blocks for synthesizing 2-substituted pyrrolidines. The opening of their oxazolidine ring by treatment with Grignard reagents has been performed and conditions for subsequent removal of the N-hydroxyethyl moiety have been found. Though the yields are moderate (36–42%), the suggested synthesis of 2-alkyl(aryl)pyrrolidines is rather simple since it does not require purification of intermediate products and is easy scalable.

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