(2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

Base Information

Chemical Name:(2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide
CAS No.:1374161-88-2
Molecular Formula:C₁₄H₂₀N₂O₂
Molecular Weight:248.325
Hs Code.:

Synonyms:(2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

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Chemical Property of (2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

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Technology Process of (2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

There total 9 articles about (2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide 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: 39.0%

: 1374161-86-0
(2R,4R)-4-hydroxy-2-methyl-2-((R)-1-phenylethylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

: 1374161-88-2
(2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 5h;
DOI:10.1002/adsc.201100028

Reference yield:

: 1374161-78-0
(2R,4R)-4-(tert-butyldimethylsilanyloxy)-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

: 1374161-88-2
(2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

Guidance literature:: Multi-step reaction with 3 steps

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

2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

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

With tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201100028

Reference yield:

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

: 1374161-88-2
(2R,4R)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid ((R)-1-phenylethyl)amide

Guidance literature:: Multi-step reaction with 8 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: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -20 - -15 °C / Inert atmosphere

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

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

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

7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

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

With 1H-imidazole; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/adsc.201100028