9-benzyl-1-methoxycarbonyl-β-carboline

Base Information

• Chemical Name: 9-benzyl-1-methoxycarbonyl-β-carboline
• CAS No.: 203717-10-6
• Molecular Formula: C₂₀H₁₆N₂O₂
• Molecular Weight: 316.359
• Mol file: 203717-10-6.mol

Synonyms:9-benzyl-1-methoxycarbonyl-β-carboline

Chemical Property of 9-benzyl-1-methoxycarbonyl-β-carboline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-benzyl-1-methoxycarbonyl-β-carboline

There total 1 articles about 9-benzyl-1-methoxycarbonyl-β-carboline 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: 88.6%

methyl 9H-pyrido[3,4-b]indole-1-carboxylate (3464-66-2) + benzyl chloride (100-44-7) → 9-benzyl-1-methoxycarbonyl-β-carboline (203717-10-6)

Guidance literature:

With sodium hydride; In N,N,N,N,N,N-hexamethylphosphoric triamide; 0 deg C to r.t., overnight;

DOI:10.1016/S0223-5234(97)89645-6

Reference yield: 72.0%

9-benzyl-1-methoxycarbonyl-β-carboline (203717-10-6) → 9-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde (203717-13-9)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃;

DOI:10.1016/S0223-5234(97)89645-6

Reference yield:

9-benzyl-1-methoxycarbonyl-β-carboline (203717-10-6) → 1-(9-Benzyl-9H-β-carbolin-1-yl)-2-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Guidance literature:

Multi-step reaction with 10 steps

1: 72 percent / DIBAL-H / toluene / -78 °C

2: 75 percent / I₂ / tetrahydrofuran; diethyl ether / 4 h / -20 deg C to r.t.

3: 80 percent / AgNO₃ / pyridine / 0.5 h / Ambient temperature

4: 93 percent / OsO₄ / pyridine; tetrahydrofuran / 3 h / Ambient temperature

5: aq. NaIO₄ / methanol / 0.5 h / Ambient temperature

6: 89 percent / CH₂Cl₂ / -20 deg C to r.t.

7: 71 percent / OsO₄ / pyridine; tetrahydrofuran / 6 h / Ambient temperature

8: 48 percent / TsOH*H₂O / acetone / 1 h / Heating

9: 82 percent / LiBH₄ / diethyl ether / 7 h / Ambient temperature

10: 71 percent / 1 M nBu₄NF, H₂O / tetrahydrofuran / 1.5 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; lithium borohydride; tetrabutyl ammonium fluoride; water; iodine; diisobutylaluminium hydride; toluene-4-sulfonic acid; silver nitrate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1016/S0223-5234(97)89645-6

upstream raw materials:

methyl 9H-pyrido[3,4-b]indole-1-carboxylate

benzyl chloride

Downstream raw materials:

9-benzyl-9H-pyrido[3,4-b]indole-1-carbaldehyde

1-(9-Benzyl-9H-β-carbolin-1-yl)-but-3-en-1-ol

9-Benzyl-1-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-9H-β-carboline

3-(9-Benzyl-9H-β-carbolin-1-yl)-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde