Borane → HCID 11096444, compound

HRID 1741813Notes

Reaction equation

HRID 1741813 reaction equation
[CH:1]1[CH:2]=[C:3]([C:10](=O)[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.B>O1CCCC1>[CH:1]1[CH:2]=[C:3]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 6331BoraneHCID 10879379Ethyl 4-(3-indolizinyl)-4-oxobutyrate

Product 1

HCID 11096444HCID 11096444, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 4-(3-indolizinyl)-4-oxobutyrate (556 mg) in tetrahydrofuran (5 ml) was added borane in tetrahydrofuran (1M solution, 3.6 ml) at 0° C. After stirring at room temperature for 10 minutes, the reaction was quenched by aqueous potassium dihydrogen phosphate at 0° C., and the resulting mixture was extracted with ether. The organic layers were washed with water, aqueous sodium bicarbonate and brine, dried over sodium sulfate. After evaporation of the solvent, the residue was chromatographed on alumina (Hexane-methylene chloride=1:1) to give ethyl 4-(3-indolizinyl)butyrate (294 mg).

Workup

  1. customthe reaction was quenched by aqueous potassium dihydrogen phosphate at 0° C.
  2. extractionthe resulting mixture was extracted with ether
  3. washThe organic layers were washed with water, aqueous sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on alumina (Hexane-methylene chloride=1:1)

Sources & evidence

ORD record
ord-f8076d5d04c8405ab1a80e5204d39e80
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

Loading…