1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate

Base Information

• Chemical Name: 1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
• CAS No.: 7128-53-2
• Molecular Formula: C₁₅H₂₁N₃O₂
• Molecular Weight: 275.351
• DSSTox Substance ID: DTXSID00859010
• Nikkaji Number: J2.708.708F
• Wikidata: Q104194838
• Metabolomics Workbench ID: 122688
• ChEMBL ID: CHEMBL11773
• Mol file: 7128-53-2.mol

Synonyms:1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate;CHEMBL11773;(3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl) N-methylcarbamate;(+)-Physostigmine;(+)Eserine;SpecPlus_000527;SCHEMBL24045;DivK1c_006623;BDBM10709;KBio1_001567;DTXSID00859010;CHEBI:182905;PIJVFDBKTWXHHD-UHFFFAOYSA-N;STL432323;AKOS022144154;N-methyl(1,8,3a-trimethylpyrrolidino[2,3-b]indolin-5-yloxy)carboxamide;NCGC00015421-03;NCGC00142456-01;FT-0673888;1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate #;1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate;1,3a,8-Trimethyl-5-(methylcarbamoyloxy)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole;7128-53-2

Chemical Property of 1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 275.16337692
• Heavy Atom Count: 20
• Complexity: 403

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C

Technology Process of 1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate

There total 30 articles about 1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl 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:

(±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole (2731-01-3,65131-82-0,65166-97-4,104069-12-7) → (+/-)-Physostigmine (57-47-6,7128-53-2,29347-10-2,69926-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HBr / 19 h / Heating

2: 48 mg / NaH / tetrahydrofuran / 1 h / 20 °C

With sodium hydride; In tetrahydrofuran; hydrogen bromide;

DOI:10.1002/chem.200601016

Reference yield:

5-(benzyloxy)-3-methyl-1H-indole (21987-24-6) → (+/-)-Physostigmine (57-47-6,7128-53-2,29347-10-2,69926-97-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / Et₃N, DMAP / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) sec-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -75 deg C, 1 h

3: 90 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

4: 58 percent / Zn, CuCl / tetrahydrofuran / 0.08 h / 0 °C

5: 84 percent / n-Bu₃SnH, AIBN / toluene / 2 h / Heating

6: 99percent HCOOH / 1 h / Ambient temperature

7: 1 h / Ambient temperature

8: -30 - 20 °C

9: H₂SO₄ / dimethylformamide / 1 h / 115 °C

10: 1.) BH₃, 2.) H₂O / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2 h

11: Raney-nickel W-2 / tetrahydrofuran / 1 h / Heating

12: 1.) Na / 1.) THF, RT, 1 min, 2.) THF, RT, 5 min

With dmap; formic acid; 2,2'-azobis(isobutyronitrile); Raney-nickel W-2; sulfuric acid; borane; water; sec.-butyllithium; tri-n-butyl-tin hydride; sodium; triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00040a013

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → (+/-)-Physostigmine (57-47-6,7128-53-2,29347-10-2,69926-97-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) EtMgBr / 1.) THF, RT, 4 h, 2.) THF, RT, 18 h

2: 98 percent / Et₃N, DMAP / tetrahydrofuran / 4 h / Ambient temperature

3: 1.) sec-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -75 deg C, 1 h

4: 90 percent / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

5: 58 percent / Zn, CuCl / tetrahydrofuran / 0.08 h / 0 °C

6: 84 percent / n-Bu₃SnH, AIBN / toluene / 2 h / Heating

7: 99percent HCOOH / 1 h / Ambient temperature

8: 1 h / Ambient temperature

9: -30 - 20 °C

10: H₂SO₄ / dimethylformamide / 1 h / 115 °C

11: 1.) BH₃, 2.) H₂O / 1.) THF, reflux, 1 h, 2.) THF, reflux, 2 h

12: Raney-nickel W-2 / tetrahydrofuran / 1 h / Heating

13: 1.) Na / 1.) THF, RT, 1 min, 2.) THF, RT, 5 min

With dmap; formic acid; 2,2'-azobis(isobutyronitrile); Raney-nickel W-2; sulfuric acid; borane; ethylmagnesium bromide; water; sec.-butyllithium; tri-n-butyl-tin hydride; sodium; triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00040a013

upstream raw materials:

(+/-)-eseroline

eseroline

methyl isocyanate

2,5-dioxopyrrolidin-1-yl methylcarbamate

Refernces

• 1、 Pinto, Artur,Jia, Yanxing,Neuville, Luc,Zhu, Jieping. "Palladium-catalyzed enantioselective domino heck-cyanation sequence: Development and application to the total synthesis of esermethole and physostigmine". . p. 961 - 967. Retrieved 2007/10/03.
• 2、 Marino,Bogdan,Kimura. "The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides". . p. 5566 - 5572. Retrieved 2007/10/02.