Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Base Information

• Chemical Name: Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate
• CAS No.: 133372-43-7
• Molecular Formula: C₂₆H₂₈N₂O₆S
• Molecular Weight: 496.584
• Mol file: 133372-43-7.mol

Synonyms:Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Chemical Property of Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

There total 3 articles about Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 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: 85.0%

Isopropylidene Derivative of Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate (133372-42-6) → Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate (133372-43-7)

Guidance literature:

With cyclohexa-1,3-diene; trifluoroacetic acid; palladium on activated charcoal; In methanol; for 12h;

DOI:10.1021/jo00311a022

Reference yield:

methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate (79328-88-4) → Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate (133372-43-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / H₂O, 4-methylmorpholine N-oxide, OsO₄ / tetrahydrofuran / 12 h

2: 87 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

3: 85 percent / cyclohexadiene, TFA / Pd / C / methanol / 12 h

With osmium(VIII) oxide; water; toluene-4-sulfonic acid; cyclohexa-1,3-diene; 4-methylmorpholine N-oxide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00311a022

Reference yield:

Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate (133372-41-5) → Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate (133372-43-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

2: 85 percent / cyclohexadiene, TFA / Pd / C / methanol / 12 h

With toluene-4-sulfonic acid; cyclohexa-1,3-diene; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo00311a022

upstream raw materials:

Isopropylidene Derivative of Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate

Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

Downstream raw materials:

Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate

20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine

Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-indol-2-yl-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate