6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline

Base Information

• Chemical Name: 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline
• CAS No.: 1499076-07-1
• Molecular Formula: C₂₅H₂₄FNO₂S
• Molecular Weight: 421.535
• Mol file: 1499076-07-1.mol

Synonyms:

Chemical Property of 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline

There total 8 articles about 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline 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:

N-((1,1-dimethyl-1H-inden-2-yl)methyl)-4-methyl-N-phenylbenzenesulfonamide (1499076-71-9) → 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline (1499076-07-1) + 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline (1499076-64-0)

Guidance literature:

With (2R,3R)-1-fluoro-4-methyl-2,3-diphenyl-1 ,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); sodium hydrogencarbonate; In nitromethane; at 20 ℃; for 1h; Overall yield = 63 %Spectr.; enantioselective reaction; Molecular sieve;

DOI:10.1002/anie.201304845

Reference yield:

3,3-dimethylindan-1-one (26465-81-6) → 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline (1499076-07-1)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

2: trichlorophosphate / 6 h / 0 - 100 °C

3: 0.25 h

4: toluene-4-sulfonic acid; benzene / 0.08 h

5: triethylamine; dmap / dichloromethane / 24 h / 20 °C

6: sodium hydrogencarbonate; (2R,3R)-1-fluoro-4-methyl-2,3-diphenyl-1 ,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) / nitromethane / 1 h / 20 °C / Molecular sieve

With dmap; sodium tetrahydroborate; (2R,3R)-1-fluoro-4-methyl-2,3-diphenyl-1 ,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; trichlorophosphate; benzene; In methanol; nitromethane; dichloromethane;

DOI:10.1002/anie.201304845

Reference yield:

benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 6a-fluoro-7,7-dimethyl-5-tosyl-6,6a,7,11b-tetrahydro-5H-indeno[2,1-c]quinoline (1499076-07-1)

Guidance literature:

Multi-step reaction with 7 steps

1: aluminum (III) chloride / 5 h / Reflux

2: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

3: trichlorophosphate / 6 h / 0 - 100 °C

4: 0.25 h

5: toluene-4-sulfonic acid; benzene / 0.08 h

6: triethylamine; dmap / dichloromethane / 24 h / 20 °C

7: sodium hydrogencarbonate; (2R,3R)-1-fluoro-4-methyl-2,3-diphenyl-1 ,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) / nitromethane / 1 h / 20 °C / Molecular sieve

With dmap; aluminum (III) chloride; sodium tetrahydroborate; (2R,3R)-1-fluoro-4-methyl-2,3-diphenyl-1 ,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; trichlorophosphate; benzene; In methanol; nitromethane; dichloromethane;

DOI:10.1002/anie.201304845

upstream raw materials:

N-((1,1-dimethyl-1H-inden-2-yl)methyl)-4-methyl-N-phenylbenzenesulfonamide

3,3-dimethylindan-1-one

3-Methylbutenoic acid

benzene