1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

Base Information

Chemical Name:1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate
CAS No.:1603824-10-7
Molecular Formula:C₂₀H₃₃NO₆
Molecular Weight:383.485
Hs Code.:

Synonyms:1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

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Chemical Property of 1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

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Technology Process of 1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

There total 1 articles about 1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-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:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 1603824-10-7
1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

: 1-(tert-butyl) 2-methyl (2S,3S,4R)-3-(2-(tert-butoxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: chloro-trimethyl-silane; triethylamine; lead(II) nitrate; citric acid / methanol; dichloromethane

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium iodide / tetrahydrofuran / 3 h / -41 °C

3.1: cerium(III) chloride bis(lithium chloride) / tetrahydrofuran / 0.25 h / -78 °C

3.2: 2 h / 78 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

4.2: 2 h / Inert atmosphere

5.1: triethylsilane / dichloromethane / 1 h / 20 °C / Inert atmosphere

6.1: dmap / dichloromethane / 20 °C

7.1: palladium diacetate; triphenylphosphine; ammonium formate / tetrahydrofuran / 0.5 h / 60 °C

With triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; chloro-trimethyl-silane; lead(II) nitrate; cerium(III) chloride bis(lithium chloride); ammonium formate; palladium diacetate; triethylamine; triphenylphosphine; citric acid; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; 1.2: |Swern Oxidation;
DOI:10.1021/acs.joc.8b00179

Reference yield:

: 1603824-10-7
1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-(tert-but-oxy)-2-oxoethyl)-4-(prop-1-en-2-yl)pyrrolidine-1,2-dicarboxylate

: 487-79-6
(-)-kainic acid

Guidance literature:: Multi-step reaction with 2 steps

1: potassium hydroxide / water; tetrahydrofuran / 17 h / 0 - 20 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

With trifluoroacetic acid; potassium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol5009526