tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate

Base Information

• Chemical Name: tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate
• CAS No.: 909135-34-8
• Molecular Formula: C₁₉H₃₂BNO₄
• Molecular Weight: 349.278
• Mol file: 909135-34-8.mol

Synonyms:tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate

Chemical Property of tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

3-Azabicyclo[3.3.1]non-6-ene-3-carboxylicacid,7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-,1,1-dimethylethylester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate

There total 10 articles about tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-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: 75.0%

tert-butyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate (909135-33-7) + bis(pinacol)diborane (73183-34-3) → tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate (909135-34-8)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; In 1,4-dioxane; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jm3011299

Reference yield:

Dimethyl 5-hydroxyisophthalate (13036-02-7) → tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate (909135-34-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Rh/Al₂O₃; hydrogen; acetic acid / methanol / 16 h / 2844.39 Torr

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C

2.2: 2 h / 0 °C

3.1: toluene-4-sulfonic acid / toluene / 3 h / Reflux

4.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - -65 °C / Inert atmosphere

5.1: dichloromethane / 0.5 h / 20 °C

6.1: palladium(II) hydroxide; ammonium formate / ethanol / 2 h / Reflux

7.1: triethylamine; dmap / dichloromethane; ethanol / 0 - 20 °C

8.1: toluene-4-sulfonic acid / acetone / 20 °C

9.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - -60 °C

9.2: 4.5 h / -78 - -10 °C

10.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; oxalyl dichloride; Rh/Al₂O₃; hydrogen; ammonium formate; potassium acetate; palladium(II) hydroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; acetone; toluene; 2.1: |Swern Oxidation;

DOI:10.1021/jm3011299

Reference yield:

5-hydroxy-cyclohexane-1,3-dicarboxylic acid dimethyl ester (113474-25-2) → tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate (909135-34-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C

1.2: 2 h / 0 °C

2.1: toluene-4-sulfonic acid / toluene / 3 h / Reflux

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 - -65 °C / Inert atmosphere

4.1: dichloromethane / 0.5 h / 20 °C

5.1: palladium(II) hydroxide; ammonium formate / ethanol / 2 h / Reflux

6.1: triethylamine; dmap / dichloromethane; ethanol / 0 - 20 °C

7.1: toluene-4-sulfonic acid / acetone / 20 °C

8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 - -60 °C

8.2: 4.5 h / -78 - -10 °C

9.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; oxalyl dichloride; ammonium formate; potassium acetate; palladium(II) hydroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; acetone; toluene; 1.1: |Swern Oxidation;

DOI:10.1021/jm3011299

upstream raw materials:

tert-butyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1]non-7-ene-3-carboxylate

bis(pinacol)diborane

Dimethyl 5-hydroxyisophthalate

5-hydroxy-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Refernces

• 1、 -. "AZABICYCLOALKANE DERIVATIVES USEFUL AS NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS". Page/Page column 36. . Retrieved 2010/11/23.