(7Br)-4,5,8,8a-tetrahydro-7-methyl-4-oxo-cyclopropa(c)pyrrolo(3,2-e)indole-2(1H)-carboxylic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: (7Br)-4,5,8,8a-tetrahydro-7-methyl-4-oxo-cyclopropa(c)pyrrolo(3,2-e)indole-2(1H)-carboxylic acid 1,1-dimethylethyl ester
• CAS No.: 127379-15-1
• Molecular Formula: C₁₇H₂₀N₂O₃
• Molecular Weight: 300.357
• DSSTox Substance ID: DTXSID10925876
• Mol file: 127379-15-1.mol

Synonyms:127379-15-1;DTXSID10925876;(7Br)-4,5,8,8a-tetrahydro-7-methyl-4-oxo-cyclopropa(c)pyrrolo(3,2-e)indole-2(1H)-carboxylic acid 1,1-dimethylethyl ester;tert-Butyl 3-methyl-8-oxo-1,4a,5,8-tetrahydrocyclopropa[c]pyrrolo[3,2-e]indole-6(4H)-carboxylate

Chemical Property of (7Br)-4,5,8,8a-tetrahydro-7-methyl-4-oxo-cyclopropa(c)pyrrolo(3,2-e)indole-2(1H)-carboxylic acid 1,1-dimethylethyl ester

Chemical Property:

• Vapor Pressure: 3.79E-10mmHg at 25°C
• Boiling Point: 500.5°Cat760mmHg
• Flash Point: 256.5°C
• Density: 1.32g/cm³
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 300.14739250
• Heavy Atom Count: 22
• Complexity: 591

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CNC2=C1C34CC3CN(C4=CC2=O)C(=O)OC(C)(C)C
• Isomeric SMILES: CC1=CNC2=C1[C@@]34CC3CN(C4=CC2=O)C(=O)OC(C)(C)C

Technology Process of (7Br)-4,5,8,8a-tetrahydro-7-methyl-4-oxo-cyclopropa(c)pyrrolo(3,2-e)indole-2(1H)-carboxylic acid 1,1-dimethylethyl ester

There total 6 articles about (7Br)-4,5,8,8a-tetrahydro-7-methyl-4-oxo-cyclopropa(c)pyrrolo(3,2-e)indole-2(1H)-carboxylic acid 1,1-dimethylethyl 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:

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate (110314-51-7) → (+)-N-BOC-CPI (127379-15-1)

Guidance literature:

With triethylamine; In water; acetonitrile; at 25 ℃; Yield given;

DOI:10.1021/ja00256a041

Reference yield:

((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol (108833-14-3) → (+)-N-BOC-CPI (127379-15-1)

Guidance literature:

Multi-step reaction with 5 steps

1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride / 1.) THF-toluene, 85 deg C

2: pyridine

3: lithium chloride / N,N-dimethyl-formamide / 80 - 100 °C

4: ammonium formate / palladium on activated charcoal / methanol

5: triethylamine / water; acetonitrile / 25 °C

With pyridine; ammonium formate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium chloride; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00256a041

Reference yield:

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6) → (+)-N-BOC-CPI (127379-15-1)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: lithium chloride / N,N-dimethyl-formamide / 80 - 100 °C

3: ammonium formate / palladium on activated charcoal / methanol

4: triethylamine / water; acetonitrile / 25 °C

With pyridine; ammonium formate; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00256a041

upstream raw materials:

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate

((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester