2-Azabicyclo[2.2.2]octane, 2-[2-[3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-1H-indol-5- yl]-2-methyl-1-oxopropyl]-

Base Information

• Chemical Name: 2-Azabicyclo[2.2.2]octane, 2-[2-[3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-1H-indol-5- yl]-2-methyl-1-oxopropyl]-
• CAS No.: 223684-20-6
• Molecular Formula: C30H39N3O
• Molecular Weight: 457.659
• Mol file: 223684-20-6.mol

Synonyms:

Chemical Property of 2-Azabicyclo[2.2.2]octane, 2-[2-[3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-1H-indol-5- yl]-2-methyl-1-oxopropyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Azabicyclo[2.2.2]octane, 2-[2-[3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-1H-indol-5- yl]-2-methyl-1-oxopropyl]-

There total 4 articles about 2-Azabicyclo[2.2.2]octane, 2-[2-[3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-1H-indol-5- yl]-2-methyl-1-oxopropyl]- 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:

{2-[5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-propyl}-carbamic acid tert-butyl ester (380227-89-4) → (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(2-aza-bicyclo[2.2.2]oct-2-yl)-2-methylpropan-1-one (223684-20-6)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(01)00512-1

Reference yield:

(S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (217192-27-3) → (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(2-aza-bicyclo[2.2.2]oct-2-yl)-2-methylpropan-1-one (223684-20-6)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. K₂CO₃ / tetrahydrofuran

2: aq. KOH / methanol / Heating

3: PyBOP; Et₃N / CH₂Cl₂

4: TFA; anisole / CH₂Cl₂

With potassium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium carbonate; methoxybenzene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(01)00512-1

Reference yield:

(S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid (217192-29-5) → (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(2-aza-bicyclo[2.2.2]oct-2-yl)-2-methylpropan-1-one (223684-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: PyBOP; Et₃N / CH₂Cl₂

2: TFA; anisole / CH₂Cl₂

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; methoxybenzene; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(01)00512-1

upstream raw materials:

{2-[5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-propyl}-carbamic acid tert-butyl ester

(S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester

(S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid

(S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester

Downstream raw materials:

N-{2-[5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-1H-indol-3-yl]-propyl}-2,4-dinitro-benzenesulfonamide