{1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester

Base Information

• Chemical Name: {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester
• CAS No.: 349609-09-2
• Molecular Formula: C₂₅H₂₈N₄O₅
• Molecular Weight: 464.521
• Mol file: 349609-09-2.mol

Synonyms:{1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester

Chemical Property of {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester

There total 12 articles about {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester 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: 99.0%

iodoacetonitrile (624-75-9) + [1,2-dihydro-8-methoxy-2-[(methylamino)-acetyl]-1-[(phenylmethoxy)methyl]-isoquinolin-7-yl]carbamic acid methyl ester (349609-18-3) → {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester (349609-09-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine;

DOI:10.1002/1521-3773(20010417)40:8<1463::AID-ANIE1463>3.0.CO;2-8

Reference yield:

2-(2-methoxyphenyl)oxirane (62717-78-6,141303-38-0) → {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester (349609-09-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: aq. NaN₃ / acetone / 3 h / Heating

2.1: NaH / tetrahydrofuran; various solvent(s) / 0.25 h / 20 °C

2.2: 13.18 g / KI / tetrahydrofuran; various solvent(s) / 2 h

3.1: 87 percent / H₂ / Pd/C / ethanol / 3 h / 20 °C

4.1: KNO₃ / CH₂Cl₂ / 48 h / -20 °C

5.1: 10.5 g / aq. LiOH / tetrahydrofuran; ethanol / 14 h

6.1: 74 percent / K₂CO₃ / acetonitrile / 120 h / Heating

7.1: 10.0 g / DMAP; pyridine / CH₂Cl₂; dimethylformamide; hexane / 0.75 h / 0 °C

8.1: H₂ / PtO₂ / tetrahydrofuran; ethanol / 16 h / 20 °C / 4137.18 Torr

9.1: aq. HCl / dioxane / 0.25 h / 90 °C

10.1: 5.22 g / pyridine / CH₂Cl₂ / 18 h / 4 °C

11.1: 94 percent / pyrrolidine / acetonitrile / 1 h / 20 °C

12.1: 99 percent / i-Pr₂NEt / tetrahydrofuran / 18 h / 20 °C

With pyrrolidine; pyridine; hydrogenchloride; dmap; lithium hydroxide; sodium azide; hydrogen; sodium hydride; potassium carbonate; potassium nitrate; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ja0174027

Reference yield:

1-[1-amino-2-(phenylmethoxy)ethyl]-2-methoxy-benzene (108343-89-1) → {1-Benzyloxymethyl-2-[2-(cyanomethyl-methyl-amino)-acetyl]-8-methoxy-1,2-dihydro-isoquinolin-7-yl}-carbamic acid methyl ester (349609-09-2)

Guidance literature:

Multi-step reaction with 9 steps

1: KNO₃ / CH₂Cl₂ / 48 h / -20 °C

2: 10.5 g / aq. LiOH / tetrahydrofuran; ethanol / 14 h

3: 74 percent / K₂CO₃ / acetonitrile / 120 h / Heating

4: 10.0 g / DMAP; pyridine / CH₂Cl₂; dimethylformamide; hexane / 0.75 h / 0 °C

5: H₂ / PtO₂ / tetrahydrofuran; ethanol / 16 h / 20 °C / 4137.18 Torr

6: aq. HCl / dioxane / 0.25 h / 90 °C

7: 5.22 g / pyridine / CH₂Cl₂ / 18 h / 4 °C

8: 94 percent / pyrrolidine / acetonitrile / 1 h / 20 °C

9: 99 percent / i-Pr₂NEt / tetrahydrofuran / 18 h / 20 °C

With pyrrolidine; pyridine; hydrogenchloride; dmap; lithium hydroxide; hydrogen; potassium carbonate; potassium nitrate; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0174027

upstream raw materials:

iodoacetonitrile

[1,2-dihydro-8-methoxy-2-[(methylamino)-acetyl]-1-[(phenylmethoxy)methyl]-isoquinolin-7-yl]carbamic acid methyl ester

2-(2-methoxyphenyl)oxirane

1-[1-amino-2-(phenylmethoxy)ethyl]-2-methoxy-benzene

Downstream raw materials:

[1,3,4,6-tetrahydro-7-methoxy-2-methyl-4-oxo-6-[(phenylmethoxy)methyl]-2H-pyrazino-[1,2-b]isoquinolin-8-yl]carbamic acid methyl ester