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

Base Information

• Chemical Name: (2S,4R)-4-hydroxy-2-[(R)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1374161-98-4
• Molecular Formula: C₁₉H₂₈N₂O₄
• Molecular Weight: 348.442
• Mol file: 1374161-98-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2S,4R)-4-hydroxy-2-[(R)-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: 91.0%

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-[(R)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester (1374161-91-7) → (2S,4R)-4-hydroxy-2-[(R)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester (1374161-98-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1002/adsc.201100028

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,4R)-4-hydroxy-2-[(R)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester (1374161-98-4)

Guidance literature:

Multi-step reaction with 6 steps

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

1.2: 18.5 h

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

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

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

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

5.2: 18 h / -20 - 20 °C / Inert atmosphere

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

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; 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:

1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate (114676-91-4) → (2S,4R)-4-hydroxy-2-[(R)-methyl-(1-phenylethyl)carbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester (1374161-98-4)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

3.2: 18 h / -20 - 20 °C / Inert atmosphere

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

With dmap; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/adsc.201100028

upstream raw materials:

(2S,4R)-4-Hydroxy-pyrrolidine-2-carbonyl chloride

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

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

di-tert-butyl dicarbonate

Downstream raw materials:

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid methyl((R)-1-phenylethyl)amide