[(8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-yl] N-methylcarbamate

Base Information

• Chemical Name: [(8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
• CAS No.: 19573-10-5
• Molecular Formula: C14H19N3O2
• Molecular Weight: 261.324
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80941346
• Nikkaji Number: J631.706E
• Pharos Ligand ID: W2XFFFFWT5H3
• ChEMBL ID: CHEMBL74089
• Mol file: 19573-10-5.mol

Synonyms:CHEMBL74089;19573-10-5;[(8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-yl] N-methylcarbamate;(-)-Norphysostigmine;(-)-N1-norphysostigmine;BDBM10687;DTXSID80941346;(3aS)-3a,8-dimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate;3a,8-Dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl hydrogen methylcarbonimidate;Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a-dimethyl-, methylcarbamate (ester), (3aS-cis)-

Chemical Property of [(8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-yl] N-methylcarbamate

Chemical Property:

• Vapor Pressure: 1.02E-06mmHg at 25°C
• Boiling Point: 403.4°C at 760 mmHg
• Flash Point: 197.8°C
• PSA: 57.09000
• Density: 1.182g/cm³
• LogP: 2.02990
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 261.147726857
• Heavy Atom Count: 19
• Complexity: 376

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCNC1N(C3=C2C=C(C=C3)OC(=O)NC)C
• Isomeric SMILES: C[C@@]12CCNC1N(C3=C2C=C(C=C3)OC(=O)NC)C

Technology Process of [(8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-yl] N-methylcarbamate

There total 11 articles about [(8bS)-4,8b-dimethyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-7-yl] N-methylcarbamate 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: 73.5%

Methyl-carbamic acid (3aS,8aR)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester (193604-43-2) → (-)-norphysostigmine (19573-10-5)

Guidance literature:

With hydrogen; trifluoroacetic acid; palladium dihydroxide; In methanol; for 1.5h; Ambient temperature;

DOI:10.1021/jm970210v

Reference yield: 72.0%

Methyl-carbamic acid (3aS,8aR)-8-formyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester (128562-54-9) → (-)-norphysostigmine (19573-10-5)

Guidance literature:

With hydrogenchloride; Ambient temperature;

Reference yield:

2-(5-methoxyindol-3-yl)ethylamine (608-07-1) → (-)-norphysostigmine (19573-10-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

2: 1.) NaH / 1.) DMSO, RT, 20 min, 2.) DMSO, 2 h

3: 77.5 percent / DMSO, 36percent aq. HCl / 1 h / Ambient temperature

4: 94.9 percent / 20percent aq. NaOH, benzyltrimethylammonium bromide / CH₂Cl₂ / 2 h / Ambient temperature

5: 75.3 percent / Red-Al / benzene / 5 h / Ambient temperature

7: 95.5 percent / BBr₃ / CHCl₃ / 4 h / Ambient temperature

8: 70.8 percent / Na / diethyl ether / 0.17 h / Ambient temperature

9: 73.5 percent / aq. TFA, H₂ / Pd(OH)2/C / methanol / 1.5 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; hydrogen; sodium; boron tribromide; trimethylbenzylammonium bromide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; chloroform; benzene;

DOI:10.1021/jm970210v

upstream raw materials:

Methyl-carbamic acid (3aS,8aR)-8-formyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

Methyl-carbamic acid (3aS,8aR)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester

2-(5-methoxyindol-3-yl)ethylamine

methyl N-[2-(5-methoxy-1H-indol-3-yl)ethyl]carbamate

Downstream raw materials:

Physostigmin