2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester
• CAS No.: 151888-65-2
• Molecular Formula: C₃₄H₃₃NO₄
• Molecular Weight: 519.64

Synonyms:2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

Chemical Property of 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester

There total 10 articles about 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic 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:

phthalic anhydride (85-44-9) → 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (151888-65-2)

Guidance literature:

Multi-step reaction with 10 steps

1: diethyl ether; benzene / Heating

2: H₂ / 5percent Pd/C / methanol / 12 h / 70 °C / 15200 Torr

3: H₂SO₄ / 4 h / Heating

4: LiBH₄ / diethyl ether / Ambient temperature

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight

7: P₂O₅ / toluene / 4 h / Heating

8: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature

9: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h

10: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight

With potassium hydroxide; lithium borohydride; sulfuric acid; hydrogen; phosphorus pentoxide; sodium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetic acid; toluene; benzene;

DOI:10.1021/jm00077a001

Reference yield:

2-(3-methyl-4-methoxybenzoyl) benzoic acid (51671-71-7) → 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (151888-65-2)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 5percent Pd/C / methanol / 12 h / 70 °C / 15200 Torr

2: H₂SO₄ / 4 h / Heating

3: LiBH₄ / diethyl ether / Ambient temperature

4: triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight

6: P₂O₅ / toluene / 4 h / Heating

7: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature

8: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h

9: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight

With potassium hydroxide; lithium borohydride; sulfuric acid; hydrogen; phosphorus pentoxide; sodium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetic acid; toluene;

DOI:10.1021/jm00077a001

Reference yield:

(4-methoxy-3-methylphenyl)magnesium bromide (117896-10-3) → 2-Diphenylacetyl-5-(4-methoxy-3-methyl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (151888-65-2)

Guidance literature:

Multi-step reaction with 10 steps

1: diethyl ether; benzene / Heating

2: H₂ / 5percent Pd/C / methanol / 12 h / 70 °C / 15200 Torr

3: H₂SO₄ / 4 h / Heating

4: LiBH₄ / diethyl ether / Ambient temperature

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 1.) NaH / 1.) EtOH, 5 min, 2.) EtOH, RT, overnight

7: P₂O₅ / toluene / 4 h / Heating

8: NaCNBH₃ / acetic acid / 0.25 h / Ambient temperature

9: 1.) KOH, 2.) sulfuric acid / 1.) methanol, reflux, 4 h, 2.) reflux, 4 h

10: 1.) diisopropylethylamine / 1.) THF, 5 min, 2.) THF, RT, overnight

With potassium hydroxide; lithium borohydride; sulfuric acid; hydrogen; phosphorus pentoxide; sodium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetic acid; toluene; benzene;

DOI:10.1021/jm00077a001

upstream raw materials:

phthalic anhydride

2-(3-methyl-4-methoxybenzoyl) benzoic acid

(4-methoxy-3-methylphenyl)magnesium bromide

[2-(4-Methoxy-3-methyl-benzyl)-phenyl]-methanol

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