(2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate
• CAS No.: 31560-21-1
• Molecular Formula: C20H21 N O6 S
• Molecular Weight: 403.44900
• DSSTox Substance ID: DTXSID90563619
• Nikkaji Number: J1.921.658F
• Wikidata: Q82448097
• Mol file: 31560-21-1.mol

Synonyms:31560-21-1;(2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate;methyl (2S,4R)-1-benzoyl-4-(4-methylphenyl)sulfonyloxypyrrolidine-2-carboxylate;(2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)-pyrrolidine-2-carboxylate;SCHEMBL10470106;DTXSID90563619;VHQQUQWNCVWPDS-AEFFLSMTSA-N;AKOS015999549;A875867;(trans)-1-Benzoyl-4-tosyloxy-L-proline methyl ester;(2S,4R)-Methyl1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate;L-Proline,1-benzoyl-4-[[(4-methylphenyl)sulfonyl]oxy]-,methyl ester,(4R)-;Methyl (4R)-1-benzoyl-4-[(4-methylbenzene-1-sulfonyl)oxy]-L-prolinate

Chemical Property of (2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate

Chemical Property:

• PSA: 98.36000
• LogP: 3.17530
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 403.10895856
• Heavy Atom Count: 28
• Complexity: 659

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)-pyrrolidine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2CC(N(C2)C(=O)C3=CC=CC=C3)C(=O)OC
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2C[C@H](N(C2)C(=O)C3=CC=CC=C3)C(=O)OC

Technology Process of (2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate

There total 4 articles about (2S,4R)-Methyl 1-benzoyl-4-(tosyloxy)pyrrolidine-2-carboxylate 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)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (31560-20-0,120806-96-4) + p-toluenesulfonyl chloride (98-59-9) → methyl (2S,4R)-1-benzoyl-4-(p-toluenesulfonyloxy)pyrrolidine-2-carboxylate (31560-21-1)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 144h;

DOI:10.1248/cpb.51.1015

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → methyl (2S,4R)-1-benzoyl-4-(p-toluenesulfonyloxy)pyrrolidine-2-carboxylate (31560-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 47.0 g / aq. NaHCO₃ / dioxane / 4 h / 20 °C

2: 91 percent / pyridine; 4-dimethylaminopyridine / 144 h / 20 °C

With pyridine; dmap; sodium hydrogencarbonate; In 1,4-dioxane;

DOI:10.1248/cpb.51.1015

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → methyl (2S,4R)-1-benzoyl-4-(p-toluenesulfonyloxy)pyrrolidine-2-carboxylate (31560-21-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: SOCl₂ / 0.5 h / -10 °C

1.2: 20 °C

2.1: 47.0 g / aq. NaHCO₃ / dioxane / 4 h / 20 °C

3.1: 91 percent / pyridine; 4-dimethylaminopyridine / 144 h / 20 °C

With pyridine; dmap; thionyl chloride; sodium hydrogencarbonate; In 1,4-dioxane;

DOI:10.1248/cpb.51.1015

upstream raw materials:

(2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

p-toluenesulfonyl chloride

(R)-4-hydroxy-L-proline ethyl ester

4R-4-hydroxyproline

Downstream raw materials:

methyl (2S,4S)-1-benzoyl-4-phenylselenopyrrolidine-2-carboxylate

(2S,4S)-(1-benzoyl-4-phenylselenopyrrolidin-2-yl)methyl benzoate

methyl (1R,2S,3S,6R,7S)-4-benzoyl-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3-carboxylate

(2S)-(1-benzoyl-3-pyrrolin-2-yl)methyl benzoate