Nitric Acid → HCID 58123826, compound

HRID 536651Notes

Reaction equation

HRID 536651 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:27])([F:26])[C:7]([N:9]1[CH2:16][CH2:15][C@:14]2([CH3:20])[C:17]([CH3:19])([CH3:18])[C@H:10]1[CH2:11][C:12]1[C:24]([OH:25])=[CH:23][CH:22]=[CH:21][C:13]=12)=[O:8]>C(O)(=O)C>[F:27][C:6]([F:5])([F:26])[C:7]([N:9]1[CH2:16][CH2:15][C@:14]2([CH3:20])[C:17]([CH3:19])([CH3:18])[C@H:10]1[CH2:11][C:12]1[C:24]([OH:25])=[C:23]([N+:1]([O-:4])=[O:2])[CH:22]=[CH:21][C:13]=12)=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 58123680HCID 58123680, compound

Product 1

HCID 58123826HCID 58123826, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Nitric acid (0.4 mL) is slowly added to a solution of 2,2,2-trifluoro-1-[(2R,6S)-10-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-ethanone (2.9 g) in acetic acid (5 mL) chilled in an ice bath. The ice bath is removed and the solution is stirred at ambient temperature overnight. The solution is poured into ice-cold water and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine and dried (Na2SO4). After removal of the solvent under reduced pressure, the residue is purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:9->1:3).

Workup

  1. temperaturechilled in an ice bath
  2. customThe ice bath is removed
  3. additionThe solution is poured into ice-cold water
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. washThe combined extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. customAfter removal of the solvent under reduced pressure
  8. customthe residue is purified by chromatography on silica gel (ethyl acetate/cyclohexane 1:9->1:3)

Sources & evidence

ORD record
ord-30822d18edb848588bd07d48514626ae
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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