(3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

Base Information

Chemical Name:(3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate
CAS No.:1455451-92-9
Molecular Formula:C₂₈H₃₃NO₈
Molecular Weight:511.572
Hs Code.:

Synonyms:(3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

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Chemical Property of (3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

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Technology Process of (3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

There total 4 articles about (3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-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: 80.0%

: 123-73-9,4170-30-3
trans-Crotonaldehyde

: 1455451-89-4
(E)-diethyl N-[2-(2-benzyloxyethyl)-4,5-methylenedioxybenzylideneamino]malonate

: 1455451-92-9
(3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: (E)-diethyl N-[2-(2-benzyloxyethyl)-4,5-methylenedioxybenzylideneamino]malonate; With (S)-diphenylprolinol; In tetrahydrofuran; at 4 ℃; for 0.5h; Inert atmosphere;

trans-Crotonaldehyde; With water; In tetrahydrofuran; at 4 ℃; for 72h; enantioselective reaction;
DOI:10.1016/j.tet.2013.08.012

Reference yield:

: 5-(2-benzyloxyethyl)-6-bromo-1,3-benzodioxole

: 1455451-92-9
(3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 6 h / -78 °C / Inert atmosphere

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

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

3.2: 72 h / 4 °C

With n-butyllithium; (S)-diphenylprolinol; sodium sulfate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2013.08.012

Reference yield:

: 119054-94-3
2-(2'-bromo-4',5'-methylenedioxyphenyl)ethanol

: 1455451-92-9
(3R,4R,5S)-diethyl 5-[6-(2-benzyloxyethyl)benzo[d][1,3]dioxol-5-yl]-4-formyl-3-methylpyrrolidine-2,2-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hydroxide / dimethyl sulfoxide / 4 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 6 h / -78 °C / Inert atmosphere

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

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

4.2: 72 h / 4 °C

With n-butyllithium; (S)-diphenylprolinol; sodium sulfate; triethylamine; potassium hydroxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tet.2013.08.012