(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Base Information

Chemical Name:(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate
CAS No.:1455451-96-3
Molecular Formula:C₃₃H₄₉NO₆Si
Molecular Weight:583.841
Hs Code.:

Synonyms:(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

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Chemical Property of (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

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Technology Process of (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

There total 7 articles about (3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-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: 91.0%

: 1455451-93-0
(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-hydroxymethyl-3-methylpyrrolidine-2,2-dicarboxylate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1455451-96-3
(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 8h; Inert atmosphere;
DOI:10.1016/j.tet.2013.08.012

Reference yield:

: 1455451-90-7
(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

: 1455451-96-3
(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium tetrahydroborate; methanol / 0 °C / Inert atmosphere

2: dmap; 1H-imidazole / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.08.012

Reference yield:

: 119367-94-1
2-<2-(Benzyloxy)ethyl>benzaldehyde

: 1455451-96-3
(3R,4R,5S)-diethyl 5-[2-(2-benzyloxyethyl)phenyl]-4-(tert-butyldimethylsilyloxymethyl)-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium sulfate; triethylamine / dichloromethane / 72 h / 20 °C / Inert atmosphere

2.1: (S)-diphenylprolinol / tetrahydrofuran / 0.5 h / 4 °C / Inert atmosphere

2.2: 72 h / 4 °C

3.1: sodium tetrahydroborate; methanol / 0 °C / Inert atmosphere

4.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; (S)-diphenylprolinol; sodium sulfate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.08.012