7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol

Base Information

• Chemical Name: 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol
• CAS No.: 886438-05-7
• Molecular Formula: C₂₁H₂₇NO₆
• Molecular Weight: 389.448
• Mol file: 886438-05-7.mol

Synonyms:7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol

Chemical Property of 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol

There total 7 articles about 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol 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:

{2-benzyloxy-1-[6-(tert-butyl-diphenyl-silanyloxy)-7-methyl-benzo[1,3]dioxol-4-yl]-ethyl}-(2,2-dimethoxy-ethyl)-amine → 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol (886438-05-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1002/anie.200503983

Reference yield:

3,4-dihydroxy-2-methylbenzaldehyde (88122-12-7) → 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol (886438-05-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Br₂; NaOAc; AcOH / 12 h / 0 - 25 °C

2.1: Cs₂CO₃ / dimethylformamide / 12 h / 105 °C

3.1: m-chloroperbenzoic acid / 3 h / 25 - 64 °C

3.2: 78 percent / HCl / 12 h / 0 - 25 °C

4.1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / 12 h / 25 °C

5.1: nBuLi / toluene; tetrahydrofuran / 0.33 h / -78 °C

5.2: 80 percent / toluene; tetrahydrofuran / 50 h / -78 °C

6.1: HCO₂H; triethylamine / Noyori (R,R)-catalyst / dimethylformamide / 24 h / 0 - 40 °C

6.2: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene; dimethylformamide / 24 h / 50 °C

6.3: H₂ / Pd/C / ethyl acetate / 15 h / 25 °C

7.1: acetic acid; NaCNBH₃; MgSO₄ / methanol / 4 h / 0 - 65 °C

8.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With dmap; n-butyllithium; formic acid; tetrabutyl ammonium fluoride; bromine; sodium acetate; sodium cyanoborohydride; magnesium sulfate; caesium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; ((1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)ruthenium chloride(I) (4-cymene); In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200503983

Reference yield:

7-bromo-4-methylbenzo[d][1,3]dioxol-5-ol (351379-53-8) → 7-[2-benzyloxy-1-(2,2-dimethoxy-ethylamino)-ethyl]-4-methyl-benzo[1,3]dioxol-5-ol (886438-05-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / 12 h / 25 °C

2.1: nBuLi / toluene; tetrahydrofuran / 0.33 h / -78 °C

2.2: 80 percent / toluene; tetrahydrofuran / 50 h / -78 °C

3.1: HCO₂H; triethylamine / Noyori (R,R)-catalyst / dimethylformamide / 24 h / 0 - 40 °C

3.2: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene; dimethylformamide / 24 h / 50 °C

3.3: H₂ / Pd/C / ethyl acetate / 15 h / 25 °C

4.1: acetic acid; NaCNBH₃; MgSO₄ / methanol / 4 h / 0 - 65 °C

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

With dmap; n-butyllithium; formic acid; tetrabutyl ammonium fluoride; sodium cyanoborohydride; magnesium sulfate; acetic acid; triethylamine; ((1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)ruthenium chloride(I) (4-cymene); In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200503983

upstream raw materials:

7-bromo-4-methylbenzo[d][1,3]dioxole-5-carbaldehyde

7-bromo-4-methylbenzo[d][1,3]dioxol-5-ol

(7-bromo-4-methyl-benzo[1,3]dioxol-5-yloxy)-tert-butyl-diphenyl-silane

2-benzyloxy-1-[6-(tert-butyl-diphenyl-silanyloxy)-7-methyl-benzo[1,3]dioxol-4-yl]-ethanone

Downstream raw materials:

{2-(5-allyloxy-9-benzyloxymethyl-6-hydroxy-4-methyl-6,9-dihydro-7H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl)-1-[3-benzyloxy-4-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methyl-benzyl]-2-oxo-ethyl}-methyl-carbamic acid tert-butyl ester

C₄₇H₅₁Cl₃N₂O₉Si

C₄₃H₄₃Cl₃N₂O₁₁

C₄₃H₄₁Cl₃N₂O₁₁