(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

Base Information

Chemical Name:(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine
CAS No.:1374647-70-7
Molecular Formula:C₂₈H₃₄N₄OSi
Molecular Weight:470.69
Hs Code.:

Synonyms:(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

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Technology Process of (2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

There total 5 articles about (2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

: 1374647-68-3
[(2R,3S)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidin-2-yl]methanol

: 1374647-70-7
(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

Guidance literature:: With tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;
DOI:10.1002/ejoc.201101829

Reference yield:

: 333969-68-9
methyl (2S,3S)-1-benzyl-3-hydroxypyrrolidine-2-carboxylate

: 1374647-70-7
(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

3: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 4 h / 0 °C / Inert atmosphere

With dmap; tetrabutylammoniun azide; diisobutylaluminium hydride; triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201101829

Reference yield:

: 4298-08-2
trans-3-hydroxy-L-proline

: 1374647-70-7
(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: thionyl chloride / 48 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

3: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

4: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

5: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 4 h / 0 °C / Inert atmosphere

With dmap; thionyl chloride; tetrabutylammoniun azide; diisobutylaluminium hydride; triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201101829