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1-Pyrrolidinecarboxylic acid, 2-[[5-[(phenylmethyl)amino]-1H-tetrazol-1-yl]methyl]-, 1,1-dimethylethyl ester, (2S)- synthesis

2synthesis methods
tert-butyl(2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate

132482-09-8
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1-Pyrrolidinecarboxylic acid, 2-[[5-[(phenylmethyl)amino]-1H-tetrazol-1-yl]methyl]-, 1,1-dimethylethyl ester, (2S)-

863671-66-3
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Yield:-

Steps:

Multi-step reaction with 3 steps
1.1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 24 h / 80 °C
2.1: 48 h / 80 °C
3.1: methylmagnesium chloride / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere
3.2: -40 - 20 °C

References:

Tymtsunik, Andriy V.;Bilenko, Vitaliy A.;Kokhan, Serhiy O.;Grygorenko, Oleksandr O.;Volochnyuk, Dmitriy M.;Komarov, Igor V. [Journal of Organic Chemistry,2012,vol. 77,# 2,p. 1174 - 1180]