Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl ester
• CAS No.: 116183-80-3
• Molecular Formula: C18H21 N O3 S
• Molecular Weight: 331.43
• DSSTox Substance ID: DTXSID10440539
• Wikidata: Q72443154
• Mol file: 116183-80-3.mol

Synonyms:116183-80-3;Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl ester;(R)-1-BENZYL-3-[(P-TOLYLSULFONYL)OXY]PYRROLIDINE;[(3R)-1-benzylpyrrolidin-3-yl] 4-methylbenzenesulfonate;(R)-1-benzyl-3-p-toluenesulfonyloxypyrrolidine;SCHEMBL3562444;DTXSID10440539;DFFINYKUAYHRBO-QGZVFWFLSA-N;AM90784;(R)-1-benzyl-3-(p-toluenesulfonyloxy)pyrrolidine;A907006;Toluene-4-sulfonicacid(R)-1-benzyl-pyrrolidin-3-ylester

Chemical Property of Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 62 °C
• Refractive Index: 1.617
• Boiling Point: 466.319°C at 760 mmHg
• PKA: 7.42±0.40(Predicted)
• Flash Point: 235.821°C
• PSA: 54.99000
• Density: 1.265g/cm³
• LogP: 3.99350
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 331.12421471
• Heavy Atom Count: 23
• Complexity: 459

Purity/Quality:

99% ^*data from raw suppliers

Toluene-4-sulfonicacid(R)-1-benzyl-pyrrolidin-3-ylester 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)OC2CCN(C2)CC3=CC=CC=C3
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@@H]2CCN(C2)CC3=CC=CC=C3

Technology Process of Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl ester

There total 6 articles about Toluene-4-sulfonic acid (R)-1-benzyl-pyrrolidin-3-yl 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:

(S)-N-benzyl-3-hydroxypyrrolidine (101385-90-4) → (3R)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine (116183-80-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / pyridine / 48 h / 10 °C

2: 1.4 g / ethyl acetate / 2 h / Heating

3: 14.6 g / aq. Na₂CO₃ / methanol / 4 h

4: pyridine / 48 h / 10 °C

With pyridine; sodium carbonate; In methanol; ethyl acetate;

DOI:10.1021/jm00100a028

Reference yield:

(3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate (116143-02-3) → (3R)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine (116183-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 14.6 g / aq. Na₂CO₃ / methanol / 4 h

2: pyridine / 48 h / 10 °C

With pyridine; sodium carbonate; In methanol;

DOI:10.1021/jm00100a028

Reference yield:

(3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine (116183-79-0) → (3R)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine (116183-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.4 g / ethyl acetate / 2 h / Heating

2: 14.6 g / aq. Na₂CO₃ / methanol / 4 h

3: pyridine / 48 h / 10 °C

With pyridine; sodium carbonate; In methanol; ethyl acetate;

DOI:10.1021/jm00100a028

upstream raw materials:

(R)-N-benzyl-3-hydroxypyrrolidine

p-toluenesulfonyl chloride

(S)-N-benzyl-3-hydroxypyrrolidine

(3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate

Downstream raw materials:

(S)-1-benzyl-3-(1-pyrrolidinyl)pyrrolidine

(3S)-1-benzyl-3-pyrrolidinamine

(3S)-(-)-1-benzyl-3-(methylamino)pyrrolidine

((S)-1-Benzyl-pyrrolidin-3-yl)-dimethyl-amine

Refernces

• 1、 -. "PIPERAZINE AND AMINOPYRROLIDINE COMPOUNDS AS HISTAMINE H3 RECEPTOR ANTAGONISTS". Page/Page column 45; 46. . Retrieved 2010/12/18.
• 2、 -. "Benzazepine and benzothiazepine derivatives". . . Retrieved 2008/06/13.