Tetrafluoroboric acid → HCID 67408768, compound

HRID 1174316Notes

Reaction equation

HRID 1174316 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3](=O)[CH2:4][CH:5]1O[N:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6]1.[H+].[B-](F)(F)(F)F>C(O)C.[Ni]>[C:2]([C:3]1[N:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=1)([CH3:17])([CH3:16])[CH3:1]

Participants

5

Reactant 2

HCID 28118Tetrafluoroboric acidHCID 67407708HCID 67407708, compound

Product 1

HCID 67408768HCID 67408768, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product from Example 115C (4.95 g, 20.5 mmol) in ethanol (400 mL) was treated with Raney nickel (20.10 g) and 48% HBF4 solution (4.13 mL), and the reaction was shaken under a hydrogen atmosphere (50 psi) at 25° C. for 1 hour. The reaction mixture was filtered, diluted with water, basified with dilute NaOH solution, and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 10% ethyl acetate in hexane to give the title compound (1.1 g, 26% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with water
  3. custompartitioned between dichloromethane and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1ec297c829d84707b086629921434a7a
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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