116103-15-2

Basic information

• Product Name: (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole
• Synonyms: (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole
• CAS NO: 116103-15-2
• Molecular Weight: 308.423
• Mol File: 116103-15-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole(116103-15-2)
• EPA Substance Registry System: (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole(116103-15-2)

Safety Data

• Hazardous Substances Data: 116103-15-2(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 104069-11-6 (3aS,8aR)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 150333-84-9 (-)-(3S)-1,3-dimethyl-5-methoxy-3-acetic acid benzylamide 
• 100-46-9 benzylamine 
• 469-22-7 eseroline 
• 74-88-4 methyl iodide 
• 150407-40-2 2-(5-methoxy-1,3-dimethyl-2-oxoindolin-3-yl)acetic acid 
• 139115-79-0 2-(5-methoxy-1,3-dimethyl-2-oxoindolin-3-yl)acetic acid 
• 129011-67-2 methyl 2,3-dihydro-5-methoxy-1,3-dimethyl-2-oxo-1H-indole-3-acetate 
• 107485-89-2 (3aS,8aS)-5-Methoxy-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid ((S)-1-phenyl-ethyl)-amide 
• 57-47-6 Physostigmin 

Downstream Products

• 116103-16-3 (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol 
• 438245-98-8 C₁₉H₂₂N₂O 
• 290294-26-7 1-benzyl-5-methoxy-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indole-8-carbaldehyde 
• 116103-17-4 N¹-benzylnorphysostigmine 
• 6091-57-2 (-)-eseramine 
• 220697-91-6 (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl-N-4'-benzyloxyphenylcarbamate 
• 219920-81-7 (-)-N¹,N⁸-bisnorcymserine 
• 145209-43-4 N¹-benzylnorphenserine 
• 290294-27-8 1-benzyl-3a-methyl-2,3,3a,8a-tetrahydro-1H-pyrrolo[2,3-b]indol-5-one 

Relevant articles and documents

Compound useful in the treatment or prevention of cognitive disorders associated with diabetes and associated methods

Described is the efficient synthesis of an easy to manipulate and utilize, soluble tartrate salt of a potent, reversible butyrylcholinesterase inhibitor, (?)-(3aS)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indol-5-yl N—4′-isopropylphenylcarbamate (“

A practical conversion of natural physostigmine into the potent butyrylcholinesterase inhibitor N1,N8-bisnorcymserine

A rapid novel synthetic route to the potent reversible butyrylcholinesterase inhibitor (-)-N1,N8-bisnorcymserine (1) is reported from physostigmine (2) in a 20% total yield. Details on the formation of the imino-quinone 6 obtained in the oxidation of N1-benzylnoresermethole (4) and its conversion into N1-bisnoreseroline (7) are given. As expected, the product of this synthesis, (1), had identical biological activity to the same agent produced by total synthesis. (C) 2000 Elsevier Science Ltd.

PROGRESS TOWARDS A PRACTICAL TOTAL SYNTHESIS OF CALABAR ALKALOIDS: TOTAL SYNTHESIS OF (-)-ESERMETHOLE AND (-)-PHYSOVENOL METHYL ETHER FROM (3S)-1,3-DIMETHYL-3-CARBOXYMETHYL-5-METHOXYOXINDOLE

Chemical resolution of the oxindoleacetic acid (7) with brucine in water yielded the acid (7a) of (3S)-absolute configuration.Acid (7a), in using conventional methods, was converted into nitrile (8a), lactone (9a) and amides (10a), and (11a) respectively.Amide (10a), on reduction with LAH in refluxing THF, directly yielded (-)-esermethole (12a), and amide (11a) similarly gave (-)-N1-benzylnoresermethole (13a).Reduction of ester (6a) with LAH in refluxing THF yielded (-)-physovenol methyl ether (14a).