(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.:1374161-93-9
Molecular Formula:C₂₅H₄₂N₂O₄Si
Molecular Weight:462.705
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 8 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: 58.0%

: 1374161-90-6
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-((S)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

: 74-88-4
methyl iodide

: 1374161-93-9
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: (2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-((S)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 - -15 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -20 - 20 ℃; for 18h; Inert atmosphere;
DOI:10.1002/adsc.201100028

Reference yield:

: 1063998-64-0
(2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride

: 1374161-93-9
(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(S)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2 h / Reflux

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

2.2: 18.5 h

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

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

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

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -20 - -15 °C / Inert atmosphere

6.2: 18 h / -20 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201100028

Reference yield:

: 74844-91-0
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

: 1374161-93-9
(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

1.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

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

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

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -20 - -15 °C / Inert atmosphere

4.2: 18 h / -20 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201100028