Sodium Carbonate → HCID 14500626, compound

HRID 1761582Notes

Reaction equation

HRID 1761582 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[C:6]1[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=1)[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].C(N1C(CC)=CC=C1[CH:45]([OH:53])C1C=CC=C(N)C=1)CCC.C([BH3-])#[N:55].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO.C(O)(=O)C>[CH2:1]([N:5]1[C:9]([CH2:10][CH3:11])=[CH:8][CH:7]=[C:6]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:45]([NH2:55])=[O:53])[CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

10

Reactant 6

HCID 10340Sodium CarbonateHCID 24436Sodium Sulfate2×HCID 5003444Sodium cyanoborohydrideHCID 14500624HCID 14500624, compoundHCID 21226445Aluminium lithium hydrideHCID 21241933HCID 21241933, compound

Product 1

HCID 14500626HCID 14500626, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 6.1 g (23 mmol) of 1-butyl-2-(3'-aminobenzoyl)-5-ethylpyrrole in 50 ml of anhydrous tetrahydrofuran was added dropwise, at room temperature, to a stirred suspension of 1 g (28 mmol) of lithium aluminum hydride in 100 ml of anhydrous tetrahydrofuran. The resulting mixture was refluxed for 15 minutes, cooled to 0° C. and the excess reagent sodium sulfate solution and solid anhydrous sodium sulfate. The insoluble material was separated by filtration and the filtrate evaporated in vacuo. The unstable crude alcohol thus obtained, 1-butyl-2-(3'-amino-α-hydroxybenzyl)-5-ethylpyrrole (6.1 g, 23 mmol) was dissolved in 75 ml of methanol, cooled to -10° C. and treated with 13 ml of glacial acetic acid and 2.8 g (44 mmol) of sodium cyanoborohydride. The reaction mixture was stirred at room temperature for 1 hour, poured into 200 ml of saturated sodium carbonate solution and the product extracted with ethyl acetate (4×300 ml). The combined extracts were washed with water (3×150 ml), dried and evaporated under reduced pressure. The residue was purified by column chromatography on 300 g of silica gel using hexane-acetone (95:5) as eluant, thus obtaining 3.5 mg (61%) of the title compound, 1-butyl-2-(3'-aminobenzyl)-5-ethylpyrrole, as an oil.

Workup

  1. temperatureThe resulting mixture was refluxed for 15 minutes
  2. customThe insoluble material was separated by filtration
  3. customthe filtrate evaporated in vacuo
  4. customThe unstable crude alcohol thus obtained
  5. temperaturecooled to -10° C.
  6. extractionthe product extracted with ethyl acetate (4×300 ml)
  7. washThe combined extracts were washed with water (3×150 ml)
  8. customdried
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on 300 g of silica gel

Sources & evidence

ORD record
ord-25e8de3ad2854b9c9ada0b12d93a6cfe
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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