(4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

Base Information

Chemical Name:(4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone
CAS No.:134272-35-8
Molecular Formula:C₂₅H₃₅NO₃Si
Molecular Weight:425.643
Hs Code.:

Synonyms:(4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

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Chemical Property of (4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

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Technology Process of (4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

There total 4 articles about (4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone 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: 41.0%

: 26905-40-8
3-methoxybenzylmagnesium chloride

: 134272-30-3
(S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-3-pyrrolin-2-one

: 134272-35-8
(4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

Guidance literature:: With copper(l) iodide; chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/0040-4020(92)85007-2

Reference yield:

: 129823-21-8,173353-34-9
(S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione

: 134272-35-8
(4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / NaBH₄ / methanol / 0.25 h / -4 °C

2: 60 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 48 percent / NaH / tetrahydrofuran / 5 h / 0 °C

4: 41 percent / CuI, TMSCl / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(92)85007-2

Reference yield:

: 253608-05-8
Acetic acid (S)-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester

: 134272-35-8
(4R,5S)-N-benzyl-5-(tert-butyldimethylsilyl)oxy-4-(3-methoxyphenyl)methyl-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 48 percent / NaH / tetrahydrofuran / 5 h / 0 °C

3: 41 percent / CuI, TMSCl / tetrahydrofuran / 1 h / -78 °C

With 1H-imidazole; copper(l) iodide; chloro-trimethyl-silane; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(92)85007-2