(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1206228-45-6
Molecular Formula:C₁₃H₁₈N₂O₂
Molecular Weight:234.298
Hs Code.:

Synonyms:(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

There total 9 articles about (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester 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: 98.0%

: 1072147-15-9
(2S,4R)-4-hydroxy-2-((R)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

: 1206228-45-6
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1016/j.tetasy.2015.09.003

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 1206228-45-6
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: thionyl chloride / methanol / 0.25 h / 0 °C

2.1: 2 h / Reflux

3.1: triethylamine / dichloromethane / 0.33 h / 20 °C

3.2: 18.5 h

4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

5.1: sodium hydroxide / methanol; water / 5 h / Reflux

6.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 °C

8.1: trifluoroacetic acid / 16 h / 20 °C

With 1H-imidazole; dmap; thionyl chloride; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201100028

Reference yield:

: 114676-91-4
1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate

: 1206228-45-6
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydroxide / methanol; water / 5 h / Reflux

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 °C

4: trifluoroacetic acid / 16 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1002/adsc.201100028