2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide

Base Information

• Chemical Name: 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide
• CAS No.: 934977-11-4
• Molecular Formula: C₂₀H₂₆BrNO₄
• Molecular Weight: 424.335
• Mol file: 934977-11-4.mol

Synonyms:2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide

Chemical Property of 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide

There total 12 articles about 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide 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%

trifluoro-methanesulfonic acid 2-(3-benzyloxy-propyl)-4-dimethylcarbamoyl-3,9-dioxa-bicyclo[4.2.1]non-7-en-7-yl ester (934977-10-3) → 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide (934977-11-4)

Guidance literature:

trifluoro-methanesulfonic acid 2-(3-benzyloxy-propyl)-4-dimethylcarbamoyl-3,9-dioxa-bicyclo[4.2.1]non-7-en-7-yl ester; With lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 3h; Heating;

With bromine; In tetrahydrofuran; dichloromethane; at -20 ℃; for 1h;

DOI:10.1021/ja068346i

Reference yield:

1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol (934977-35-2) → 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide (934977-11-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

1.2: 100 percent / tetrahydrofuran / 4 h / 20 °C

2.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

3.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

4.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

5.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

6.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

7.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

8.1: 98 percent / NaH / tetrahydrofuran / 12 h / 20 °C

9.1: 92 percent / NMO / TPAP / CH₂Cl₂ / 3 h / 20 °C

10.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -78 °C

10.2: 94 percent / toluene; tetrahydrofuran / 1 h / -78 °C

11.1: lithium chloride / Pd(PPh₃)4 / tetrahydrofuran / 3 h / Heating

11.2: 75 percent / Br₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

With tetrachloromethane; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; TOP; potassium hexamethylsilazane; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene;

DOI:10.1021/ja068346i

Reference yield:

2-[1-(3-benzyloxy-propyl)-2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide (934977-36-3) → 2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-7-ene-4-carboxylic acid dimethylamide (934977-11-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

2.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

3.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

4.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

5.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

6.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

7.1: 98 percent / NaH / tetrahydrofuran / 12 h / 20 °C

8.1: 92 percent / NMO / TPAP / CH₂Cl₂ / 3 h / 20 °C

9.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -78 °C

9.2: 94 percent / toluene; tetrahydrofuran / 1 h / -78 °C

10.1: lithium chloride / Pd(PPh₃)4 / tetrahydrofuran / 3 h / Heating

10.2: 75 percent / Br₂ / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

With tetrachloromethane; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; TOP; potassium hexamethylsilazane; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetone; toluene;

DOI:10.1021/ja068346i

upstream raw materials:

trifluoro-methanesulfonic acid 2-(3-benzyloxy-propyl)-4-dimethylcarbamoyl-3,9-dioxa-bicyclo[4.2.1]non-7-en-7-yl ester

2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoic acid methyl ester

2-(3-benzyloxy-propyl)-7-oxo-3,9-dioxa-bicyclo[4.2.1]nonane-4-carboxylic acid dimethylamide

2-(3-benzyloxy-propyl)-7-hydroxy-3,9-dioxa-bicyclo[4.2.1]nonane-4-carboxylic acid dimethylamide

Downstream raw materials:

1-[2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-4-yl]-propan-1-one

1-[2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-4-yl]-propan-1-one

2-(3-benzyloxy-propyl)-7-bromo-4-(1-bromo-propyl)-3,9-dioxa-bicyclo[4.2.1]nonane

1-[2-(3-benzyloxy-propyl)-7-bromo-3,9-dioxa-bicyclo[4.2.1]non-4-yl]-propan-1-ol