Borane → HCID 69314316, compound

HRID 1394050Notes

Reaction equation

HRID 1394050 reaction equation
[CH2:1]([C@H:8]([NH2:26])[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:13][CH2:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>C1COCC1>[CH2:1]([C@H:8]([NH2:26])[CH2:9][N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:15][CH2:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 69309205HCID 69309205, compound

Product 1

HCID 69314316HCID 69314316, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 5, Step (b) (0.1 g) was dissolved in THF (3 ml) and borane [0.84 ml (1M in THF)] was added. The reaction was stirred for 1 hr and then quenched slowly with methanol. The solvents were evaporated and the residue re-dissolved in 50% H2O/50% conc HCl (2 ml) and refluxed for 1 hr. The solvents were evaporated. The free base was liberated by addition of aqueous NaOH (2M) and extraction with ethyl acetate followed by drying, filtration and evaporation of solvent to give the sub-title compound as an oil (0.092 g).

Workup

  1. customquenched slowly with methanol
  2. customThe solvents were evaporated
  3. dissolutionthe residue re-dissolved in 50% H2O/50% conc HCl (2 ml)
  4. temperaturerefluxed for 1 hr
  5. customThe solvents were evaporated
  6. additionThe free base was liberated by addition of aqueous NaOH (2M) and extraction with ethyl acetate
  7. customby drying
  8. filtrationfiltration and evaporation of solvent

Sources & evidence

ORD record
ord-8e44c5d666574e1c81b245ff6addb44d
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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