Trifluoroacetic acid → HCID 59837845, compound

HRID 1727189Notes

Reaction equation

HRID 1727189 reaction equation
CO[N:3]=[CH:4][CH:5]1[CH:11]([CH:12]=NOC)[CH:10]2[CH2:16][CH:6]1[CH2:7][N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9]2.F[C:25](F)(F)C(O)=O.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[C:18]1([CH2:17][N:8]2[CH2:7][CH:6]3[CH2:16][CH:10]([C:11]4[C:5]3=[CH:4][N:3]=[CH:25][CH:12]=4)[CH2:9]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 131727288HCID 131727288, compound

Product 1

HCID 59837845HCID 59837845, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-(phenylmethyl)-3-azabicyclo[3.2.1]octane-6,7-dicarbaldehye bis (O-methyloxime) (Preparation 33, 5.0 g, 15.2 mmol) in dichloroethane (150 ml) was added trifluoroacetic acid (17 ml) and the reaction mixture was stirred under nitrogen at room temperature for 20 min. The reaction mixture was heated under reflux for 2 h and then concentrated to give a brown oil. Ethyl acetate (100 ml) was added and the solution was treated with saturated sodium carbonate solution (70 ml) the layers were separated and the organic layer washed with brine and dried (Na2SO4) and concentrated to give an oil (4.0 g). The crude oil was purified by flash chromatography using silica gel eluting with ethyl acetate to give the title compound as an orange oil (1.93 g, 51%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. concentrationconcentrated
  4. customto give a brown oil
  5. customwere separated
  6. washthe organic layer washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-034b250abf894010866022d28dbc51a7
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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