Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester
• CAS No.: 77784-53-3
• Molecular Formula: C₂₄H₂₆N₂O₂
• Molecular Weight: 374.483
• Mol file: 77784-53-3.mol

Synonyms:Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester

Chemical Property of Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester

There total 1 articles about Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl 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: 46.0%

Methyl-[(4S,5S)-5-(2-oxo-propyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester (75303-71-8,75303-72-9) + Methylenetriphenylphosphorane (19493-09-5) → Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester (77784-53-3)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

Reference yield: 70.0%

Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester (77784-53-3) → [(4S,5S)-5-(2,3-Dihydroxy-2-methyl-propyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-methyl-carbamic acid benzyl ester (77784-54-4)

Guidance literature:

With osmium(VIII) oxide; In pyridine; diethyl ether; at 0 - 20 ℃;

Reference yield:

Methyl-[(4S,5S)-5-(2-methyl-allyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester (77784-53-3) → Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester (77784-56-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / OsO₄ / diethyl ether; pyridine / 0 - 20 °C

2: 100 percent / pyridine

3: 25 percent / p-TsOH / benzene / Heating

4: 1.) 2percent KOH, 2.) Na / 1.) t-BuOH, H₂O, 55-60 deg, 2.) liq. NH₃, THF

5: 1.) Et₃N, 2.) 3.5percent KOH / 1.) CH₂Cl₂, pyridine, 2.) a) t-BuOH, H₂O, 55-60 deg, b) pyridine

With potassium hydroxide; osmium(VIII) oxide; sodium; toluene-4-sulfonic acid; triethylamine; In pyridine; diethyl ether; benzene;

upstream raw materials:

Methyl-[(4S,5S)-5-(2-oxo-propyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid benzyl ester

Methylenetriphenylphosphorane

Downstream raw materials:

[(4S,5S)-5-(2,3-Dihydroxy-2-methyl-propyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-methyl-carbamic acid benzyl ester

(+/-)-chanoclavine I

Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester

Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester