210841-59-1

Basic information

• Product Name: 1H-Pyrrole-2-carboxylicacid,5-propyl-,methylester(9CI)
• Synonyms: 1H-Pyrrole-2-carboxylicacid,5-propyl-,methylester(9CI)
• CAS NO: 210841-59-1
• Molecular Formula: C9H13NO2
• Molecular Weight: 167.21
• Product Categories: GLYCINESCAFFOLD
• Mol File: 210841-59-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrole-2-carboxylicacid,5-propyl-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2-carboxylicacid,5-propyl-,methylester(9CI)(210841-59-1)
• EPA Substance Registry System: 1H-Pyrrole-2-carboxylicacid,5-propyl-,methylester(9CI)(210841-59-1)

Safety Data

• Hazardous Substances Data: 210841-59-1(Hazardous Substances Data)

Upstream product

• 1000682-46-1 C₉H₁₃N₃O₂ 
• 210841-49-9 methyl (E)-2-(N-benzhydrylideneamino)oct-4-enoate 
• 405551-15-7 methyl (E)-2-aminooct-4-enoate 
• 210841-58-0 methyl (E)-2-(4-tolylsulfonylamino)oct-4-enoate 
• 120989-95-9 ethyl (E)-hex-2-en-1-yl carbonate 
• 928-95-0 (E)-2-Hexen-1-ol 

Relevant articles and documents

A new approach to 5-substituted prolines and 2-pyrrolecarboxylates

Iodocyclisations of the allylic glycinates 7 lead either to the trans- or cis-2,5-disubstituted proline derivatives 8 or 9, depending on the reaction conditions; subsequent treatment of these with DBU in DMF gives the 2-pyrrolecarboxylates 10 and 13 in excellent yields by a double elimination of hydrogen iodide and toluenesulfinic acid.

Transition metal-catalyzed synthesis of pyrroles from dienyl azides

(Chemical Equation Presented) A range of 2,5-disubstituted and 2,4,5-trisubstituted pyrroles can be synthesized from dienyl azides at room temperature using catalytic amounts of Znl2 or Rh2(O 2CC3F7)4.

The synthesis of 5-substituted proline derivatives and of 5-substituted pyrrole-2-carboxylates by 5-endo cyclisations featuring a method for effectively favouring these with respect to 5-exo cyclisations

Overall 5-endo cyclisations of the C-allylic glycine sulfonamides 5 lead to usually excellent yields of the 2,5-cis- or 2,5-trans-pyrrolidine-2-carboxylates 11 and 12 respectively, depending upon whether base is absent or present. While reductions to the corresponding pyrrolidine-2-methanols 13 proved efficient, subsequent eliminations of the elements of hydrogen iodide gave mixtures of products 14-16. Suitably positioned hydroxy groups compete successfully with the sulfonamide via a 5-exo cyclisation mode. However, when such a substrate contains a furan ring attached to the alkene function (21), then cyclisation does occur at the sulfonamide, presumably by participation of the furan oxygen, to give an iodopyrrolidine-2-methanol 13a. Finally, base-induced elimination of both hydrogen iodide and toluene-p-sulfinic acid from the initial iodopyrrolidines 11 and 12 leads to 5-substituted pyrrole-2-carboxylates 26. Overall, this sequence is complementary to the Kenner pyrrole synthesis.