146681-75-6

Basic information

• Product Name: 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester
• Synonyms: 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester
• CAS NO: 146681-75-6
• Molecular Weight: 352.433
• Mol File: 146681-75-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester(146681-75-6)
• EPA Substance Registry System: 2-[3-(2-Benzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester(146681-75-6)

Safety Data

• Hazardous Substances Data: 146681-75-6(Hazardous Substances Data)

Upstream product

• 146681-79-0 N_b,N_b-dibenzyl-2-<(benzoyloxy)methyl>tryptamine 
• 146681-76-7 Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate 
• 146681-77-8 N_b,N_b-dibenzyl-2-(ethoxycarbonyl)tryptamine 
• 146681-80-3 N_b,N_b-dibenzyl-2-(cyanomethyl)tryptamine 
• 146681-78-9 N_b,N_b-dibenzyl-2-(hydroxymethyl)tryptamine 
• 100-44-7 benzyl chloride 
• 53590-32-2 3-(2-aminoethyl)-1H-indole-2-carboxylic acid ethyl ester hydrochloride 
• 146681-81-4 2-[3-(2-Dibenzylamino-ethyl)-1H-indol-2-yl]-3-hydroxy-propionic acid methyl ester 

Downstream Products

• 18374-17-9 (±)-vincadifformine 
• 89117-97-5 methyl 4-acetyl-3-benzyl-1,2,3,3a,4,5-hexahydro-7H-pyrrolo(2,3-d)carbazole-6-carboxylate 
• 122698-20-8 11-((ethoxycarbonyl)methyl)-1-benzyl-2,3,8,10,11,11a-hexahydro-1H-pyrrolo[2,3-d]carbazole-9-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of Vinca Alkaloids and Related Compounds. 63. A New Synthetic Pathway for Preparing Alkaloids and Related Compounds with the Aspidosperma Skeleton. Total Syntheses of (+/-)-Vincadifformine, (+/-)-Tabersonine, and (+/-)-3-Oxotabersonine

Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of (2-ethoxycarbonyl)tryptamine (2).The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43).The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tricyclic benzoate esters 37 and 38.The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.