Sodium hydride → Pyrrole

HRID 1719880Notes

Reaction equation

HRID 1719880 reaction equation
[CH2:1]([C:9]1[NH:10][C:11]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)=[CH:12][CH:13]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[NH:10]1[CH:11]=[CH:12][CH:13]=[CH:9]1.[C:27]([O:31][C:32]([N:10]1[C:11]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)=[CH:12][CH:13]=[C:9]1[CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 13451132HCID 13451132, compound

Product 2

HCID 8027PyrroleHCID 13505280HCID 13505280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound (V) is dissolved in a suspension of an ethereal or dipolar solvent, preferably in dry dimethylformamide, and mixed with sodium hydride. The mixture is heated to 45°-60° for 1-3 hours, preferably 2 hours. Suitable N-protecting agent R2, such as aroylchloride, alkanoylchloride, alkylchloroformate, preferably di-t-butylcarbonate, is added and the mixture is stirred at 60°-70° for 1-3 hours. After purification and crystallization of methods known in the art, ±1-R2 -protected-2-[phenethyl]-5-[3,4-methylenedioxy)benzoyl]pyrrole, preferably 1-t-butoxycarbonyl-2-[phenethyl]-5-[(3,4-methylenedioxy)benzoyl]pyrrole (VI) is obtained.

Workup

  1. temperatureThe mixture is heated to 45°-60° for 1-3 hours, preferably 2 hours
  2. customAfter purification and crystallization of methods

Sources & evidence

ORD record
ord-637cfa108c17433085774ca764216664
Source dataset
uspto-grants-1985_09
Patent number
US04543361

Reaction notes

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