Sodium Carbonate → HCID 14500646, compound

HRID 1761593Notes

Reaction equation

HRID 1761593 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1)[CH2:8][CH2:9][CH3:10].C(N1C=CC=C1[CH:34]([OH:42])C1C=CC=C(N)C=1)CCC.C([BH3-])#[N:44].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CO.C(O)(=O)C>[CH2:7]([N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:34]([NH2:44])=[O:42])[CH:18]=1)[CH2:8][CH2:9][CH3:10]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 14500643HCID 14500643, compoundHCID 14500644HCID 14500644, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14500646HCID 14500646, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 5 g (130 mmol) of lithium aluminum hydride in 500 ml of anhydrous tetrahydrofuran was added dropwise, at room temperature, a solution of 16 g (66 mmol) of 1-butyl-2-(3'-aminobenzoyl)pyrrole in 100 ml of anhydrous tetrahydrofuran. The reaction mixture was refluxed for 30 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. The unstable crude alcohol thus obtained, 1-butyl-2-(3'-amino-α-hydroxybenzyl)pyrrole (16 g, 66 mmol), was immediately dissolved in 250 ml of methanol, cooled to 0° C. and treated with 66 ml of glacial acetic acid and 10.1 g (160 mmol) of sodium cyanoborohydride. The reaction mixture was stirred at room temperature for 11/2 hours, poured into 1000 ml of saturated sodium carbonate solution and the product extracted with ethyl acetate (3×500 ml). The combined extracts were washed with water (2×300 ml) dried and evaporated in vacuo. The residue was purified by column chromatography on 750 g of silica gel using hexane-ethyl acetate (80:20) as eluant, thus obtaining 7.6 g (50%) of the title compound, 1-butyl-2-(3'-aminobenzyl)pyrrole, as an oil.

Workup

  1. additionwas added dropwise, at room temperature
  2. temperatureThe reaction mixture was refluxed for 30 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
  6. customThe unstable crude alcohol thus obtained
  7. temperaturecooled to 0° C.
  8. extractionthe product extracted with ethyl acetate (3×500 ml)
  9. washThe combined extracts were washed with water (2×300 ml)
  10. customdried
  11. customevaporated in vacuo
  12. customThe residue was purified by column chromatography on 750 g of silica gel

Sources & evidence

ORD record
ord-20bc507d46e340aca16d64424545d8a8
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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