(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

Base Information

Chemical Name:(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate
CAS No.:1415906-48-7
Molecular Formula:C₂₄H₃₇NO₆Si
Molecular Weight:463.646
Hs Code.:

Synonyms:(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

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Chemical Property of (2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

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Technology Process of (2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

There total 4 articles about (2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate 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: 28.0%

: 4122-53-6
1-(1H-imidazol-1-yl)-2-methylpropan-1-one

: 114358-14-4
O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

: 1415906-48-7
(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

: 1415906-49-8
(2R,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

Guidance literature:: (2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 2.5h; Inert atmosphere;

1-(1H-imidazol-1-yl)-2-methylpropan-1-one; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.25h; Overall yield = 47 %; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2012.10.076

Reference yield: 27.0%

: 79-30-1
isobutyryl chloride

: 114358-14-4
O₁-benzyl O₂-methyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxypyrrolidine-1,2-dicarboxylate

: 1415906-48-7
(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

: 1415906-49-8
(2R,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

Guidance literature:: (2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 2.5h; Inert atmosphere;

isobutyryl chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.25h; Overall yield = 38 %; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetlet.2012.10.076

Reference yield:

: 64187-48-0
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

: 1415906-48-7
(2S,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

: 1415906-49-8
(2R,4R)-1-benzyl 2-methyl 4-(tert-butyldimethylsilyloxy)-2-isobutyrylpyrrolidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / 23 h / 20 °C / Inert atmosphere

2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; hexane / 2.5 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 °C / Inert atmosphere

2.3: 0.25 h / -78 - 0 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1016/j.tetlet.2012.10.076