Borane;tetrahydrofuran → HCID 18408982, compound

HRID 993254Notes

Reaction equation

HRID 993254 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:10][C:11]#[N:12])[CH2:9][CH2:8]2)[CH:2]=1.B.C1COCC1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:10][CH2:11][NH2:12])[CH2:8][CH2:9]2)[CH:2]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 184089671-(3-Pyridinyl)cyclopropaneacetonitrile

Product 1

HCID 18408982HCID 18408982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 7-4 (31.3 g, 198 mmol) in 200 mL anhydrous THF was added borane-THF solution (1.5M, 660 mL, 990 mol). The reaction mixture was stirred at room temperature overnight. It was then quenched with methanol gradually until no gas was released. Then additional methanol (150 ml) was added, followed by 30 mL of 6N HCl. The mixture was stirred for 1 hr and concentrated to a viscous residue. It was then treated with 6N NaOH until pH >11 and stirred for 30 min and extracted four times with CHCl3. After solvent removal, the residue was purified using silica gel chromatography (100%EtOAc to 50% EtOAc/46% EtOH/2% NH4OH/2% H2O) to obtain the desired product 7-5 as an oil.

Workup

  1. customIt was then quenched with methanol gradually until no gas
  2. additionThen additional methanol (150 ml) was added
  3. stirringThe mixture was stirred for 1 hr
  4. concentrationconcentrated to a viscous residue
  5. additionIt was then treated with 6N NaOH until pH >11
  6. stirringstirred for 30 min
  7. extractionextracted four times with CHCl3
  8. customAfter solvent removal
  9. customthe residue was purified

Sources & evidence

ORD record
ord-5a92856909ff4cf1bc6d1a5bbf4b23a3
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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