65166-97-4

Basic information

• Product Name: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole
• Synonyms: esermethole
• CAS NO: 65166-97-4
• Molecular Formula: C₁₄H₂₀N₂O
• Molecular Weight: 232.3214
• Mol File: 65166-97-4.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 348.1°C at 760 mmHg
• Flash Point: 103.8°C
• Density: 1.087g/cm³
• Vapor Pressure: 5.14E-05mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole(65166-97-4)
• EPA Substance Registry System: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole(65166-97-4)

Safety Data

• Hazardous Substances Data: 65166-97-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole" is a complex organic molecule with a fused bicyclic ring structure. It consists of a pyrroloindole core with a methoxy group attached to the 5th carbon, and three methyl groups attached to the 1st, 3rd, and 8th carbons. (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole has potential pharmaceutical importance due to its structural novelty and the presence of a methoxy group, which can influence its biological activity. The unique arrangement of atoms in this molecule may give it interesting biological properties, making it a potential candidate for further pharmacological investigation.

Upstream product

• 131042-90-5 (3S)-1,3-dimethyl-3-{β-[(methoxycarbonyl)amino]ethyl}-5-methoxyoxindole 
• 1010-68-0 1,3-dimethyl-5-hydroxyoxindole 
• 50-00-0 formaldehyd 
• 131101-14-9 (3S)-1,3-dimethyl-3-(β-aminoethyl)-5-methoxyoxindole 
• 46479-70-3 (+/-)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 63483-09-0 4-chloro-2-methyl-butanal 
• 116707-99-4 1,3-dimethyl-5-methoxyindolin-2-one 
• 593-51-1 methylamine hydrochloride 
• 153109-52-5 (3S)-(5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetaldehyde 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 157496-75-8 tert-butyl (2-iodo-4-methoxyphenyl)carbamate 
• 1426832-63-4 C₁₅H₂₁NO₃ 
• 128368-43-4 2-isopropenyl-4-methoxyaniline 
• 128368-44-5 (2-Isopropenyl-4-methoxy-phenyl)-carbamic acid methyl ester 

Downstream Products

• 57-47-6 (+/-)-Physostigmine 
• 104069-12-7 (3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 101246-66-6 phenserine 
• 29347-15-7 (+)-Eseroline 
• 104015-32-9 (3S)-1,3-dimethyl-3-<2'-(dimethylamino)ethyl>-5-hydroxyindoline 
• 57-47-6 Physostigmin 
• 139314-01-5 (3aS,cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 70354-71-1 (+/-)-eseroline 
• 104015-30-7 (3S)-1,3-dimethyl-3-<2'-(dimethylamino)ethyl>-5-methoxyindoline 
• 469-22-7 eseroline 

Relevant articles and documents

Ethylene in organic synthesis: A new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation

The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3, 3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides

This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in up to 90% yield and up to 97:3 e.r. This methodology was applied to the total synthesis of (-)-esermethole and (-)-phenserine.

Generation of All-Carbon Quaternary Stereocenters at the C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement and Revision of Absolute Configuration: Total Synthesis of (-)-Physostigmine

A diastereoselective (up to >99%) route to all carbon quaternary stereocenters at the C-3 position of cyclic lactams has been developed via Johnson-Claisen rearrangement of ?-hydroxy-α,β-unsaturated lactams. It has been observed that olefin geometry plays an important role in the development of the absolute stereochemistry of the product. Dependence of product configuration on the olefin geometry is explained by postulating probable transition states. The success of this method has been shown for multigram-scale synthesis of these substituted lactams from commercially available cheap starting materials. The synthetic usefulness of this method is also demonstrated by carrying out the total synthesis of (a-)-physostigmine.

Pd(0)-Catalyzed Chemoselective Deacylative Alkylations (DaA) of N-Acyl 2-Oxindoles: Total Syntheses of Pyrrolidino[2,3- b]indoline Alkaloids, (±)-Deoxyeseroline, and (±)-Esermethole

We report an efficient Pd(0)-catalyzed deacylative allylation of N-acyl 3-substituted 2-oxindoles via the coupling of in situ generated nucleophiles (3 and 4) with allyl electrophiles for the synthesis of a variety of 2-oxindoles with C3-quaternary centers. Gratifyingly, this alkylation process is found to be highly chemoselective in nature, where a C-C bond formation is completely predominant over a C-N bond formation. A variety of key intermediates were synthesized utilizing an aforementioned methodology.