HCID 14500616, compound → HCID 21241960, compound

HRID 1761576Notes

Reaction equation

HRID 1761576 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[C:11]1[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1)[CH2:8][CH3:9]>O1CCCC1>[CH2:7]([N:10]1[C:14]([CH2:15][CH3:16])=[CH:13][CH:12]=[C:11]1[CH:17]([OH:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1)[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 14500616HCID 14500616, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21241960HCID 21241960, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 2 g (50 mmol) of lithium aluminum hydride in 100 ml of anhydrous tetrahydrofuran was added dropwise, at room temperature, a solution of 12 g (46 mmol) of 1-propyl-2-(3'-aminobenzoyl)-5-ethylpyrrole in 100 ml of anhydrous tetrahydrofuran. The reaction mixture was refluxed for 15 minutes, cooled to 0° C. and the excess reagent destroyed by carefully adding ethyl acetate, saturated sodium sulfate solution and solid anhydrous sodium sulfate. The insoluble material was separated by filtration and the filtrate evaporated in vacuo, to produce 11.1 g (43 mmol) of 1-propyl-2-(3'-amino-α-hydroxybenzyl)-5-ethylpyrrole. This crude compound was dissolved in 150 ml of methanol, cooled to -10° C. and treated with 23.5 ml of glacial acetic acid and 5.1 g (80 mmol) of sodium cyanoborohydride. The reaction mixture was warmed to room temperature and stirred for 18 additional hours. It was then poured into 500 ml of saturated sodium carbonate solution and the product extracted with ethyl acetate (4×300 ml). The combined extracts were washed with water (3×300 ml), dried and evaporated in vacuo. The residue was purified by column chromatography on 500 g of silica gel, using hexane-acetone (97:3) as eluant, thus obtaining 4.8 g (47%) of the title compound, 1-propyl- 2-(3'-aminobenzyl)-5-ethylpyrrole, as an oil.

Workup

  1. additionwas added dropwise, at room temperature
  2. temperatureThe reaction mixture was refluxed for 15 minutes
  3. customthe excess reagent destroyed by carefully adding ethyl acetate, saturated sodium sulfate solution and solid anhydrous sodium sulfate
  4. customThe insoluble material was separated by filtration
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-0aac634b899d4334a604426b8ed33416
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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