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

Base Information

• Chemical Name: methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate
• CAS No.: 79328-88-4
• Molecular Formula: C₃₁H₂₈N₂O₆S
• Molecular Weight: 556.639
• Mol file: 79328-88-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-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: 84.0%

N-benzyloxycarbonyl-1,2-dihydropyridine (79328-85-1) + methyl α-methylene-1-(phenylsulfonyl)-1H-indole-2-acetate (74185-41-4) → methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate (79328-88-4)

Guidance literature:

at 100 ℃; for 60h;

DOI:10.1016/S0040-4020(98)00289-0

Reference yield:

pyridine (110-86-1) → methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate (79328-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaBH₄ / ethanol / 1.5 h / -78 °C

2: 73 percent / 96 h / 100 °C

With sodium tetrahydroborate; In ethanol;

DOI:10.1021/jo00337a003

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate (79328-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaBH₄ / ethanol / 1.5 h / -78 °C

2: 73 percent / 96 h / 100 °C

With sodium tetrahydroborate; In ethanol;

DOI:10.1021/jo00337a003

upstream raw materials:

N-benzyloxycarbonyl-1,2-dihydropyridine

methyl α-methylene-1-(phenylsulfonyl)-1H-indole-2-acetate

pyridine

benzyl chloroformate

Downstream 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

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-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate