70354-71-1

Basic information

• Product Name: (+/-)-eseroline
• Synonyms: (+/-)-eseroline
• CAS NO: 70354-71-1
• Molecular Weight: 218.299
• Mol File: 70354-71-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (+/-)-eseroline(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-eseroline(70354-71-1)
• EPA Substance Registry System: (+/-)-eseroline(70354-71-1)

Safety Data

• Hazardous Substances Data: 70354-71-1(Hazardous Substances Data)

Upstream product

• 2731-01-3 (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole 
• 1238046-59-7 C₇H₁₃NO₃ 
• 2555-05-7 3-methyl-2-pyrrolidinone 
• 104069-10-5 (+)-N¹-noreseroline O-methyl ether 
• 153109-55-8 (R)-5-Methoxy-1,3-dimethyl-3-((E)-2-triisopropylsilanyloxy-vinyl)-1,3-dihydro-indol-2-one 
• 153109-56-9 (R)-3-(2-oxoethyl)-1,2-dihydro-5-methoxy-1,3-dimethyl-2-oxo[3H]indole 
• 153109-51-4 (Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid (2-iodo-4-methoxy-phenyl)-methyl-amide 
• 153109-50-3 (Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid 
• 139115-75-6 2-iodo-4-methoxy-N-methylaniline 
• 29347-10-2 physostigmine 
• 104069-12-7 (3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 

Downstream Products

• 57-47-6 (+/-)-Physostigmine 
• 29347-10-2 physostigmine 
• 101246-66-6 phenserine 
• 103957-95-5 (+)-physostigmine salicylate 
• 93185-42-3 O-(chloroethyl)eseroline 
• 29347-11-3 (+)-physovenine 
• 136173-08-5 (3aR,8aR)-5-methoxy-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole 
• 136173-09-6 (+)-(3aR)-3a,8-dimethyl-2,3,3a,8a-tetrahydrofuro[2,3-b]indol-5-ol 

Relevant articles and documents

Synthesis of (+)-phenserine using an interrupted Fischer indolization reaction

A concise synthesis of the Alzheimer's therapeutic (+)-phenserine is described. The approach features an interrupted Fischer indolization to construct the pyrrolidinoindoline core, in addition to a classical resolution to arrive at phenserine in enantioenriched form.

Palladium-catalyzed enantioselective domino heck-cyanation sequence: Development and application to the total synthesis of esermethole and physostigmine

An efficient synthesis of functionalized 3-alkyl-3-cyanomethyl-2-oxindole 1 by a palladium-catalyzed domino Heck-cyanation reaction has been developed. Reaction of ortho-iodoanilide 5 with potassium ferro(II)cyanide, K 4[Fe(CN)6], dissolved in DMF in the presence of palladium acetate and sodium carbonate afforded oxindole 1 in good to excellent yields. An enantioselective domino Heck-cyanation process has been developed for the first time using (S)-DIFLUORPHOS as a chiral supporting ligand, and an enantioselectivity of up to 79% ee in the enantiomerically enriched oxindole was obtained under optimized conditions. A concise total synthesis of esermethole and physostigmine, powerful inhibitors of acetyl- and butyryl-cholinesterase, is documented.

2-Azonianorbornene-2-spiro-1'-aziridinium triflate - A novel ethylene immonium ion equivalent: Application to a synthesis of physostigmine

A unique protocol for either the aminoethylation or the N-methyl aminoethylation of carbonyl compounds featuring the preparation and use of a novel spiroaziridinium salt, 2-azonianorbornene-2-spiro-1'-aziridinium triflate 2, is described.