(2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine

Base Information

Chemical Name:(2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine
CAS No.:1318128-57-2
Molecular Formula:C₁₈H₃₀N₄OSi
Molecular Weight:346.548
Hs Code.:

Synonyms:(2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)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 (2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine

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Technology Process of (2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine

There total 6 articles about (2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)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:

: 635299-82-0
(3S,5S)-1-benzyl-3-(tert-butyldimethylsilyloxy)-5-hydroxymethylpyrrolidine

: 1318128-57-2
(2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine

: 1318128-54-9
(3R,5S)-3-azido-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine

Guidance literature:: With tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at 0 ℃; for 2.5h;
DOI:10.1021/ol201769b

Reference yield:

: 1318129-56-4
(2S,4S)-methyl 1-benzyl-4-(phenylcarbonyloxy)pyrrolidine-2-carboxylate

: 1318128-57-2
(2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine

: 1318128-54-9
(3R,5S)-3-azido-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: methanol; potassium hydroxide / 0.5 h / 20 °C

2.1: thionyl chloride / 16 h / Reflux

3.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 1 h / 0 °C

4.2: 1 h / 0 - 20 °C

5.1: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 2.5 h / 0 °C

With methanol; dmap; thionyl chloride; tetrabutylammoniun azide; diisobutylaluminium hydride; triethylamine; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; potassium hydroxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol201769b

Reference yield:

: 1318129-60-0
(2S,4S)-methyl 1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carboxylate

: 1318128-57-2
(2S,4S)-2-(azidomethyl)-1-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine

: 1318128-54-9
(3R,5S)-3-azido-1-benzyl-5-(tert-butyldimethylsilyloxy)piperidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; dichloromethane / 1 h / 0 °C

1.2: 1 h / 0 - 20 °C

2.1: tetrabutylammoniun azide; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate / dichloromethane / 2.5 h / 0 °C

With tetrabutylammoniun azide; diisobutylaluminium hydride; ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol201769b