2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide

Base Information

• Chemical Name: 2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide
• CAS No.: 104465-74-9
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.375

Synonyms:2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide

Chemical Property of 2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide

Chemical Property:

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Technology Process of 2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide

There total 1 articles about 2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide 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: 70.0%

2-(phenylmethyl)isoquinoline-1,3(2H,4H)-dione (21640-31-3) + ethyl bromoacetate (105-36-2) → 2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide (104465-74-9)

Guidance literature:

With sodium t-butanolate; In tert-butyl alcohol; for 6h; Ambient temperature;

DOI:10.1021/jo00374a035

Reference yield: 85.0%

2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide (104465-74-9) → 2-benzyl-4-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (23007-65-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; di-isopropyl ether; for 24h;

DOI:10.1021/jo00374a035

Reference yield:

2-benzyl-4-<(ethoxycarbonyl)methyl>homophthalimide (104465-74-9) → (+/-)-isocyclocelabenzine (104595-98-4,70503-72-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / LiAlH₄ / tetrahydrofuran; diisopropyl ether / 24 h

2: concd. hydrochloric acid, H₂ / 20percent Pd/C / methanol / 24 h / 20 °C / 760 Torr

3: 75 percent / sodium acetate / ethanol / 2 h / Heating

4: 90 percent / 2 h / 100 °C

5: 95 percent / KMnO₄, H₂O / acetone / 1 h / Ambient temperature

6: 95 percent / H₂ / platinum oxide / CHCl₃; ethanol / 8 h / 20 °C / 760 Torr

7: 86 percent / 1-methyl-2-chloropyridinium iodide, triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

8: 90 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

9: 75 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

10: 0.5 h / Ambient temperature

11: 5percent aq. NaHCO₃

12: NaBH₄ / methanol / 1 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; potassium permanganate; lithium aluminium tetrahydride; 2-chloro-1-methyl-pyridinium iodide; water; hydrogen; sodium acetate; sodium hydrogencarbonate; potassium carbonate; triethylamine; pyridinium chlorochromate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; di-isopropyl ether; acetone;

DOI:10.1021/jo00374a035

upstream raw materials:

2-(phenylmethyl)isoquinoline-1,3(2H,4H)-dione

ethyl bromoacetate

Downstream raw materials:

2-benzyl-4-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline

2-(1,2,3,4-tetrahydroisoquinolin-4-yl)ethanol

(Z)-8-Phenyl-1,5,9-triaza-tricyclo[10.7.1.0^13,18]icosa-9,13,15,17-tetraene-6,19-dione

2-<8-(tert-butoxycarbonyl)-5-oxo-7-phenyl-4,8-diazaoctyl>-4-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinolin-1-one

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