2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene

Base Information

• Chemical Name: 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene
• CAS No.: 316129-49-4
• Molecular Formula: C₁₈H₂₃NO₄S
• Molecular Weight: 349.451
• Mol file: 316129-49-4.mol

Synonyms:2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene

Chemical Property of 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene

There total 5 articles about 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene 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: 63.0%

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + 1-acetyl-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene (316129-48-3) → 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene (316129-49-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; for 19h;

DOI:10.1021/jo001147b

Reference yield:

t-3,4-N-tosylaziridino-t-1,2-methylene-r-(2-phenylsulfonyl)cyclohexane → 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene (316129-49-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / BF₃*Et₂O / CH₂Cl₂; nitromethane / 45 h / -78 - 20 °C

2: 91 percent / DBU / 3.5 h / 20 °C

3: 98 percent / aq. H₂O₂; K₂CO₃ / methanol / 23 h / 20 °C

4: 87 percent / t-BuOK / tetrahydrofuran / 0.92 h / 20 °C

5: 63 percent / Me₃SiOTf / CH₂Cl₂ / 19 h / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; nitromethane; dichloromethane;

DOI:10.1021/jo001147b

Reference yield:

3-(phenylsulfonyl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]-2-octene (177980-54-0) → 2-(2-methyl-1,3-dioxolan-2-yl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene (316129-49-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / DBU / 3.5 h / 20 °C

2: 98 percent / aq. H₂O₂; K₂CO₃ / methanol / 23 h / 20 °C

3: 87 percent / t-BuOK / tetrahydrofuran / 0.92 h / 20 °C

4: 63 percent / Me₃SiOTf / CH₂Cl₂ / 19 h / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; dihydrogen peroxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo001147b

upstream raw materials:

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

1-acetyl-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]oct-2-ene

3-(phenylsulfonyl)-8-[(4-methylphenyl)sulfonyl]-8-azabicyclo[3.2.1]-2-octene

2-acetyl-8-[(4-methylphenyl)sulfonyl]-3-(phenylsulfonyl)-8-azabicyclo[3.2.1]octane

Downstream raw materials:

8-Methyl-2-(methylcarbonyl)-8-azabicyclo<3.2.1>oct-2-ene