O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate

Base Information

• Chemical Name: O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate
• CAS No.: 312327-47-2
• Molecular Formula: C₂₇H₃₄N₂O₆Si
• Molecular Weight: 510.662
• Mol file: 312327-47-2.mol

Synonyms:O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate

Chemical Property of O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate

There total 11 articles about O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate 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: 76.0%

O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate (312327-46-1) + methyl iodide (74-88-4) → O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate (312327-47-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

DOI:10.1021/jo001080s

Reference yield:

7-bromo-benzo[1,3]dioxole-5-carbaldehyde (19522-96-4) → O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate (312327-47-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / PTSA / benzene / 24 h / Heating

2: 96 percent / Pd₂(dba)3; (S)-BINAP; t-BuONa / toluene / 3 h / 90 °C

3: 100 percent / PPTS; water / acetone / 0.5 h / Heating

4: Amberlyst A-21 ion-exchange resin / tetrahydrofuran / 3 h / 20 °C

5: 1.15 g / 2,6-lutidine / tetrahydrofuran / 2 h / 0 - 20 °C

6: 95 percent / NH₄⁽¹⁺⁾*HCO₂^(1-) / Pd/C / methanol; tetrahydrofuran / 1 h / Heating

7: 91 percent / DMAP; K₂CO₃ / tetrahydrofuran / -78 - -30 °C

8: 84 percent / trimethyl orthoformate / 12 h / Heating

9: 67 percent / diphenyl ether / 0.33 h / 240 °C

10: 76 percent / K₂CO₃ / dimethylformamide / 3 h / 100 °C

With 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; Amberlyst A-21 ion-exchange resin; water; ammonium formate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate; trimethyl orthoformate; palladium on activated charcoal; In tetrahydrofuran; methanol; diphenylether; N,N-dimethyl-formamide; acetone; toluene; benzene; 1: cyclocondensation / 2: Substitution / 3: Hydrolysis / 4: Addition / 5: silylation / 6: Hydrogenolysis / 7: benzyloxycarbonylation / 8: Condensation / 9: Cyclization / 10: Methylation;

DOI:10.1021/jo001080s

Reference yield:

3-bromo-4,5-dihydroxybenzaldehyde (16414-34-9) → O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[9-methyl-1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate (312327-47-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / KF / dimethylformamide / 4 h / 140 °C

2: 98 percent / PTSA / benzene / 24 h / Heating

3: 96 percent / Pd₂(dba)3; (S)-BINAP; t-BuONa / toluene / 3 h / 90 °C

4: 100 percent / PPTS; water / acetone / 0.5 h / Heating

5: Amberlyst A-21 ion-exchange resin / tetrahydrofuran / 3 h / 20 °C

6: 1.15 g / 2,6-lutidine / tetrahydrofuran / 2 h / 0 - 20 °C

7: 95 percent / NH₄⁽¹⁺⁾*HCO₂^(1-) / Pd/C / methanol; tetrahydrofuran / 1 h / Heating

8: 91 percent / DMAP; K₂CO₃ / tetrahydrofuran / -78 - -30 °C

9: 84 percent / trimethyl orthoformate / 12 h / Heating

10: 67 percent / diphenyl ether / 0.33 h / 240 °C

11: 76 percent / K₂CO₃ / dimethylformamide / 3 h / 100 °C

With 2,6-dimethylpyridine; dmap; potassium fluoride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; Amberlyst A-21 ion-exchange resin; water; ammonium formate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate; trimethyl orthoformate; palladium on activated charcoal; In tetrahydrofuran; methanol; diphenylether; N,N-dimethyl-formamide; acetone; toluene; benzene; 1: cyclocondensation / 2: cyclocondensation / 3: Substitution / 4: Hydrolysis / 5: Addition / 6: silylation / 7: Hydrogenolysis / 8: benzyloxycarbonylation / 9: Condensation / 10: Cyclization / 11: Methylation;

DOI:10.1021/jo001080s

upstream raw materials:

O-benzyl N-2-(tert-butyldimethylsilyloxy)-2-[1,3-dioxolo[4,5-h]-6(9H)-quinolinon-6-yl]ethyl carbamate

methyl iodide

7-bromo-benzo[1,3]dioxole-5-carbaldehyde

3-bromo-4,5-dihydroxybenzaldehyde