Pyrrole → HCID 58843361, compound

HRID 501912Notes

Reaction equation

HRID 501912 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.C([O:11][C@@H:12]1[C@@H:17]([O:18]C(=O)C)[C@H:16]([O:22]C(=O)C)[C@@H:15]([CH2:26][O:27]C(=O)C)[O:14][C@H:13]1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37]Br)[CH:32]=1)(=O)C.C[O-].[Na+]>CN(C)C=O.O1CCCC1.CO>[N:3]1([CH2:37][C:33]2[CH:32]=[C:31]([C@@H:13]3[O:14][C@H:15]([CH2:26][OH:27])[C@@H:16]([OH:22])[C@H:17]([OH:18])[C@H:12]3[OH:11])[CH:36]=[CH:35][CH:34]=2)[CH:7]=[CH:6][CH:5]=[CH:4]1

Participants

8

Reactant 4

HCID 8027PyrroleHCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 58843512HCID 58843512, compound

Product 1

HCID 58843361HCID 58843361, compoundYield 35.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (42 mg) was added to a solution of pyrrole (64 mg) in dimethylformamide (10 ml) under cooling with ice, and the mixture was stirred for half an hour at room temperature. After the mixture was cooled to −30° C., a solution of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-(bromomethyl)phenyl]-D-glucitol (80 mg) in tetrahydrofuran (2 ml) was added dropwise thereto, and the resultant was stirred for one hour at room temperature. Methanol (10 ml) and sodium methoxide (44 mg) was added thereto, and the resultant was stirred for one hour at the same temperature. After the completion of the reaction, the reaction mixture was concentrated to give the residue. The resulting residue was purified by a reversed-phase column chromatography (water-methanol) to obtain (1S)-1,5-anhydro-1-[3-(1H-pyrrole-1-ylmethyl)-phenyl]-D-glucitol (18 mg).

Workup

  1. temperatureunder cooling with ice
  2. temperatureAfter the mixture was cooled to −30° C.
  3. stirringthe resultant was stirred for one hour at room temperature
  4. stirringthe resultant was stirred for one hour at the same temperature
  5. customAfter the completion of the reaction
  6. concentrationthe reaction mixture was concentrated
  7. customto give the residue
  8. customThe resulting residue was purified by a reversed-phase column chromatography (water-methanol)

Sources & evidence

ORD record
ord-1bdd07a29529442a9f0334fee6d66270
Source dataset
uspto-grants-2010_08
Patent number
US07772407B2

Reaction notes

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