(R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine

Base Information

• Chemical Name: (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine
• CAS No.: 1215272-30-2
• Molecular Formula: C₂₀H₂₀Cl₂FNO₃S
• Molecular Weight: 444.354
• Mol file: 1215272-30-2.mol

Synonyms:

Chemical Property of (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine

There total 8 articles about (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine 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: 12.0%

4-methanesulfonyl-phenol (14763-60-1) + (1R,2R)-4,6-dichloro-1-((R)-3-fluoropyrrolidin-1-yl)indan-2-ol → (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine (1215272-30-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acs.jmedchem.6b00624

Reference yield:

3-(2,4-dichlorophenyl)propionic acid (55144-92-8) → (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine (1215272-30-2)

Guidance literature:

Multi-step reaction with 7 steps

1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 6 h

2: aluminum (III) chloride / dichloromethane / 3 h / 0 °C / Reflux

3: sodium tetrahydroborate / ethanol / 10 - 20 °C

4: toluene-4-sulfonic acid / toluene / Dean-Stark; Reflux

5: 4-(3-phenylpropyl)pyridine-N-oxide; (S,S)-(+)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride / dichloromethane

6: acetonitrile / 80 °C

7: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

With aluminum (III) chloride; sodium tetrahydroborate; oxalyl dichloride; (S,S)-(+)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; triphenylphosphine; 4-(3-phenylpropyl)pyridine-N-oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7: |Mitsunobu Displacement;

DOI:10.1021/acs.jmedchem.6b00624

Reference yield:

3-(2,4-dichlorophenyl)propanoyl chloride (52397-82-7) → (R)-1-[(1S,2S)-4,6-dichloro-1-(4-methanesulfonylphenoxy)indan-2-yl]-3-fluoropyrrolidine (1215272-30-2)

Guidance literature:

Multi-step reaction with 6 steps

1: aluminum (III) chloride / dichloromethane / 3 h / 0 °C / Reflux

2: sodium tetrahydroborate / ethanol / 10 - 20 °C

3: toluene-4-sulfonic acid / toluene / Dean-Stark; Reflux

4: 4-(3-phenylpropyl)pyridine-N-oxide; (S,S)-(+)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride / dichloromethane

5: acetonitrile / 80 °C

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

With aluminum (III) chloride; sodium tetrahydroborate; (S,S)-(+)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; triphenylphosphine; 4-(3-phenylpropyl)pyridine-N-oxide; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; 6: |Mitsunobu Displacement;

DOI:10.1021/acs.jmedchem.6b00624

upstream raw materials:

4-methanesulfonyl-phenol

3-(2,4-dichlorophenyl)propionic acid

3-(2,4-dichlorophenyl)propanoyl chloride

4,6-dichloroindan-1-ol

Refernces

• 1、 -. "SUBSTITUTED AMINOINDANES AND ANALOGS THEREOF, AND THE PHARMACEUTICAL USE THEREOF". Page/Page column 68; 95. . Retrieved 2011/09/14.