Dimethylformamide → HCID 22038294, compound

HRID 1790431Notes

Reaction equation

HRID 1790431 reaction equation
C([Li])CCC.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](Br)[CH:26]=3)[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].CN(C)[CH:31]=[O:32].[Cl-].[NH4+]>CCCCCC.O1CCCC1.C(OCC)(=O)C>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([CH2:31][OH:32])[CH:26]=3)[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22038034HCID 22038034, compoundHCID 178418339Butyllithium

Product 1

HCID 22038294HCID 22038294, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 2.5 M solution (16 ml) of n-butyllithium in hexane was added dropwise at ±78° C. into a solution of 1-[1-(t-butoxycarbonyl)piperidin-4-yl]-6-bromoindoline (10 g) in tetrahydrofuran (250 ml) over 5 mm. After 10 mm, dimethylformamide (3.0 ml) was added and the resultant mixture was allowed to warm to room temperature. Next, a saturated aqueous solution of ammonium chloride and ethyl acetate were added thereto and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue were added ethanol (50 ml) and sodium borohydride (1.0 g) and the resultant mixture was stirred at room temperature for 30 mm. Then ice water and ethyl acetate were added to the reaction solution and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (7.9 g) (yield: 91%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue were added ethanol (50 ml) and sodium borohydride (1.0 g)
  6. additionThen ice water and ethyl acetate were added to the reaction solution
  7. customthe layers were separated
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-7d9016fa0d5b4078bf455b179cad85f1
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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