(3S,4R)-1-benzyl-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,4R)-1-benzyl-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid
• CAS No.: 1268519-99-8
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Mol file: 1268519-99-8.mol

Synonyms:(3S,4R)-1-benzyl-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid

Chemical Property of (3S,4R)-1-benzyl-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-benzyl-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid

There total 2 articles about (3S,4R)-1-benzyl-4-(ethoxycarbonyl)pyrrolidine-3-carboxylic acid 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:

(E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → (3S*,4S*)-1-benzyl-pyrrolidine-3,4-dicarboxylic acid monoethyl ester (1268519-99-8,895243-39-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 48.5h;

Reference yield:

N-benzyl-N-(methoxymethyl)trimethyl-silylamine + (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) → (3S*,4S*)-1-benzyl-pyrrolidine-3,4-dicarboxylic acid monoethyl ester (1268519-99-8,895243-39-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 48.5h;

Reference yield:

(3S*,4S*)-1-benzyl-pyrrolidine-3,4-dicarboxylic acid monoethyl ester (1268519-99-8,895243-39-7) → N-{(3S*,4S*)-4-[(cyclopropanecarbonyl-methyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide dihydrochloride

Guidance literature:

Multi-step reaction with 12 steps

1.1: hydrogen / palladium(II) hydroxide/carbon / ethanol / 5 h

2.1: dimethylsulfide borane complex / tetrahydrofuran / 4.33 h / -10 - 20 °C

3.1: Dess-Martin periodane / dichloromethane; water

4.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 4.42 h

5.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 2 h / Heating / reflux

6.1: methanol; lithium hydroxide; water / 0 °C

7.1: dimethylsulfide borane complex / tetrahydrofuran / -10 - 20 °C

8.1: Dess-Martin periodane / dichloromethane; water

9.1: magnesium sulfate / tetrahydrofuran / 20 °C

9.2: 1 h

10.1: triethylamine / dichloromethane / 20 °C

11.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C

12.1: hydrogenchloride / 1,4-dioxane

With hydrogenchloride; methanol; lithium hydroxide; dimethylsulfide borane complex; water; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium tris(acetoxy)borohydride; magnesium sulfate; Dess-Martin periodane; triethylamine; trifluoroacetic acid; palladium(II) hydroxide/carbon; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 1,2-dichloro-ethane;

upstream raw materials:

(E)-4-ethoxy-4-oxobut-2-enoic acid

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine