(3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid
• CAS No.: 1001179-54-9
• Molecular Formula: C₁₆H₁₉Cl₂NO₄
• Molecular Weight: 360.237
• Mol file: 1001179-54-9.mol

Synonyms:(3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid

Chemical Property of (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid

There total 5 articles about (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)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: 81.0%

tert-butyl (3S,4R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate (1160262-39-4) → (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid (1001179-54-9,1160260-94-5)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 60h;

Reference yield:

(3S,4R)-1-tert-butyl 3-methyl 4-(3,4-dichlorophenyl)pyrrolidine-1,3-dicarboxylate (1001179-51-6) → (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid (1001179-54-9,1160260-94-5)

Guidance literature:

(3S,4R)-1-tert-butyl 3-methyl 4-(3,4-dichlorophenyl)pyrrolidine-1,3-dicarboxylate; With methanol; lithium hydroxide; water; at 20 ℃; for 6h;

With hydrogenchloride; In methanol; water;

Reference yield:

methyl 3-(3,4-dichlorophenyl)-2-propenoate (82475-75-0) → (3S,4R)-1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylic acid (1001179-54-9,1160260-94-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / dichloromethane / -5 - 20 °C

1.3: pH 14

2.1: carbonochloridic acid 1-chloro-ethyl ester / 1,2-dichloro-ethane / 1 h / 0 °C / Heating / reflux

3.1: triethylamine / tetrahydrofuran / 20 °C

4.1: methanol; lithium hydroxide; water / 6 h / 20 °C

With methanol; lithium hydroxide; carbonochloridic acid 1-chloro-ethyl ester; water; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

upstream raw materials:

(3S,4R)-1-tert-butyl 3-methyl 4-(3,4-dichlorophenyl)pyrrolidine-1,3-dicarboxylate

tert-butyl (3S,4R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate

(3S,4R)-methyl 4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

(3S,4R)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester

Downstream raw materials:

tert-butyl (3S,4R)-3-amino-4-(3,4-dichlorophenyl)pyrrolidine-1-carboxylate