141870-92-0

Basic information

• Product Name: dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• Synonyms: dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate
• CAS NO: 141870-92-0
• Molecular Weight: 430.481
• Mol File: 141870-92-0.mol

Chemical Properties

• CAS DataBase Reference: dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate(141870-92-0)
• EPA Substance Registry System: dimethyl (2S,3aR,8aS)-2-methyl-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate(141870-92-0)

Safety Data

• Hazardous Substances Data: 141870-92-0(Hazardous Substances Data)

Upstream product

• 136057-11-9 dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate 
• 74-88-4 methyl iodide 
• 79631-04-2 N_α-methoxycarbonyl-D-tryptophan methyl ester 
• 79465-82-0 L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole 

Downstream Products

• 1064604-54-1 C₂₁H₂₁BrN₂O₆S 
• 141870-93-1 (+)-(2S,3aR,8aS)-1-(Methoxycarbonyl)-2-methyl-8-(phenylsulfonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid 
• 143100-48-5 (S)-3-(1-Benzenesulfonyl-1H-indol-3-yl)-2-methoxycarbonylamino-2-methyl-propionic acid methyl ester 
• 141870-94-2 (2S,3aR,8aS)-8-Benzenesulfonyl-2-isobutoxycarbonyloxycarbonyl-2-methyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 

Relevant articles and documents

Synthesis of α-[14C]methyl and α-[3H]-L-tryptophan

The title compounds were synthesized starting from dimethyl (2S,3aR,8aS)-(+)-8-(phenylsulfonyl)hexahydropyrrolo[2,3-b]indole-1,2-d icarboxylate. This compound on treatment with LDA followed by reaction with [14C]methyl iodide or [3H]

Conformational analysis of substituted hexahydropyrrolo [2,3-b]indoles and related systems. An unusual example of hindered rotation about sulfonamide S-N bonds. An X-ray crystallographic and NMR study

An indepth comparison of the solution (CDCl3, 1H-NMR) and solid state (X-ray) conformations of the hexahydropyrrolo[2,3-b]indoles 4, 5, and 6 is made. Close parallels with the literature conformations of the aflatoxin furo[2,3-b]benzofuran skeleton and with the conformation of the naturally occurring hexahydropyrrolindole physostigmine are noted. In the solid state the sulfonamide N in 4-6 is non-planar with various degrees of rotation about the S-N bond. In solution, variable temperature 1H-NMR evidence indicates hindered rotation about the N-S bond of the sulfonamide group in 4-6, possibly coupled to inversion of the pyramidal sulfonamide N atom. Reaction of 5 with LDA followed by quenching with methyl iodide resulted in alkylation with clean inversion of configuration.

Preparation, Isolation and X-Ray Crystallographic Structure Determination of a Stable, Crystalline Carbonic Anhydride of an N-Protected α-Amino Acid

The reaction of methyl (2S,3aR,8aS)-2-carboxy-8-phenylsulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo-indole-1-carboxylate and isobutyl chloroformate in tetrahydrofuran at -15 deg C in the presence of trimethylamine results in the formation of the correspo

ENANTIOSPECIFIC SYNTHESIS OF AMINO ACIDS: PREPARATION OF (R)- AND (S)-α-METHYLASPARTIC ACID FROM (S)-TRYPTOPHAN

The enantiospecific synthesis of both antipodes of α-methylaspartic acid from (S)-tryptophan is described with the key steps being alkylation of the hexahydropyrroloindole 4, oxidative degradation of indoles and, for the preparation of the (R)-isomer, Barton reductive decarboxylation.