(2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

Base Information

Chemical Name:(2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine
CAS No.:642410-73-9
Molecular Formula:C₂₀H₃₃NO₃Si
Molecular Weight:363.572
Hs Code.:

Synonyms:(2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

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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,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

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Technology Process of (2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

There total 7 articles about (2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine 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: 80.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 599191-14-7
(2S,5S)-N-(benzyloxycarbonyl)-2-hydroxymethyl-5-methylpyrrolidine

: 642410-73-9
(2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

Guidance literature:: With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 15h;
DOI:10.1002/ejoc.200300393

Reference yield:

: (S)-2-(1-Ethoxy-ethoxymethyl)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester

: 642410-73-9
(2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 58 percent / nBuLi / tetrahydrofuran; hexane / -72 °C

2.1: 63 percent / sodium amalgam; NaHPO₄ / methanol / 20 °C

3.1: 89 percent / H₂ / Pd(OH)2 / methanol / 20 °C / 760 Torr

4.1: aq. HCl / tetrahydrofuran / 3 h / 20 °C

4.2: Na₂CO₃ / CH₂Cl₂; H₂O

5.1: 80 percent / IMIDAZOLE / CH₂Cl₂; dimethylformamide / 15 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium amalgam; n-butyllithium; camphor-10-sulfonic acid; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300393

Reference yield:

: 599191-11-4
tert-butyl (1S)-1-[(1-ethoxyethoxy)methyl]-4-oxopentylcarbamate

: 642410-73-9
(2S,5S)-N-(benzyloxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / H₂ / Pd(OH)2 / methanol / 20 °C / 760 Torr

2.1: aq. HCl / tetrahydrofuran / 3 h / 20 °C

2.2: Na₂CO₃ / CH₂Cl₂; H₂O

3.1: 80 percent / IMIDAZOLE / CH₂Cl₂; dimethylformamide / 15 h / 20 °C

With 1H-imidazole; hydrogenchloride; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300393