79465-87-5

Basic information

• Product Name: DIMETHYL L-(+)-TETRAHYDROPYRROLO(2,3-B)INDOLE-1,2-DICARBOXYLATE
• Synonyms: DIMETHYL L-(+)-TETRAHYDROPYRROLO(2,3-B)INDOLE-1,2-DICARBOXYLATE;dimethyl tetrahydropyrrolo[2,3-b]indole-1,2-dicarboxylate
• CAS NO: 79465-87-5
• Molecular Formula: C14H16 N2 O4
• Molecular Weight: 0
• Mol File: 79465-87-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DIMETHYL L-(+)-TETRAHYDROPYRROLO(2,3-B)INDOLE-1,2-DICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL L-(+)-TETRAHYDROPYRROLO(2,3-B)INDOLE-1,2-DICARBOXYLATE(79465-87-5)
• EPA Substance Registry System: DIMETHYL L-(+)-TETRAHYDROPYRROLO(2,3-B)INDOLE-1,2-DICARBOXYLATE(79465-87-5)

Safety Data

• Hazardous Substances Data: 79465-87-5(Hazardous Substances Data)

Upstream product

• 66377-68-2 N_b-methoxycarbonyl-DL-tryptophan methyl ester 

Downstream Products

• 67811-39-6 DL-(2β,3aα,8aα)-8-acetyl-1,2-dimethoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 

Relevant articles and documents

Formation and Reactions of the Cyclic Tautomers of Tryptophans and Tryptamines. VII. Hydroxylation of Tryptophans and Tryptamines

The 5-hydroxytryptophan derivative 12 was prepared in 60percent yield from the tryptophan derivative 8 by selective oxidation of the cyclic tautomer 9 with Fremy's salt or Pb(OAc)4-CF3COOH to the p-quinoneimine 10, followed by reduction and ring-opening.By analogous oxidation, serotonin was prepared from tryptamine.On the other hand, the oxidation of the Na-acetyl-cyclic tautomers (16 and 22) with Pb(OAc)4-CF3COOH followed by methylation gave the 5- and 6-methoxy derivatives (17, 18, 23, and 24) in 20-40percent yields.These compounds were readily converted to the 5- and 6-methoxytryptophan derivatives (20, 21) by acid treatment.These methods are the first practical hydroxylation procedures to be reported for tryptophans.Keywords: 5-hydroxytryptophan; methoxytryptophan; cyclic tautomer; tryptophan; oxidation; hydroxylation; lead tetraacetate; Fremy's salt.

CYCLIC TAUTOMERS OF TRYPTOPHANS AND TRYPTAMINES-4; SYNTHESIS OF CYCLIC TAUTOMERS OF TRYPTOPHANS AND TRYPTAMINES

Nb-Methoxycarbonyltryptophan methyl ester (DL- and L-13) was cyclized to the corresponding trans cyclic tautomer (14) in excellent yield in various acids such as 85percent phosphoric acid or trifluoroacetic acid.The cis cyclic tautomer (15) was formed as the less stable and kinetically controlled product and converted to the more stable trans isomer (14) under the reaction condition.The trans isomer (14) was reverted to 13 on treatment with 10percent sulfuric acid in methanol.Other tryptophan and tryptamine derivatives (6 and 19a) also cyclized to the corresponding cyclic tautomers in similar acidic media.