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

Base Information

Chemical Name:(3R,4R,5S)-diethyl 4-(tert-butyldimethylsilyloxymethyl)-5-[2-(2-hydroxyethyl)phenyl]-3-methylpyrrolidine-2,2-dicarboxylate
CAS No.:1455451-99-6
Molecular Formula:C₂₆H₄₃NO₆Si
Molecular Weight:493.716
Hs Code.:

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

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

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

There total 7 articles about (3R,4R,5S)-diethyl 4-(tert-butyldimethylsilyloxymethyl)-5-[2-(2-hydroxyethyl)phenyl]-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: 81.0%

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

: 1455451-99-6
(3R,4R,5S)-diethyl 4-(tert-butyldimethylsilyloxymethyl)-5-[2-(2-hydroxyethyl)phenyl]-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: With methanol; palladium 10% on activated carbon; hydrogen; at 20 ℃; for 24h;
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

: 1455451-99-6
(3R,4R,5S)-diethyl 4-(tert-butyldimethylsilyloxymethyl)-5-[2-(2-hydroxyethyl)phenyl]-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: methanol; palladium 10% on activated carbon; hydrogen / 24 h / 20 °C

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.08.012

Reference yield:

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

: 1455451-99-6
(3R,4R,5S)-diethyl 4-(tert-butyldimethylsilyloxymethyl)-5-[2-(2-hydroxyethyl)phenyl]-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 5 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

5.1: methanol; palladium 10% on activated carbon; hydrogen / 24 h / 20 °C

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; (S)-diphenylprolinol; palladium 10% on activated carbon; hydrogen; sodium sulfate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2013.08.012