Triethylamine → 1-Benzyl-4-(4-fluorophenyl)-l-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate

HRID 497920Notes

Reaction equation

HRID 497920 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]1[CH2:20][CH:19]=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:17]([CH2:28]O)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:30][C:31]([F:44])([F:43])[S:32]([O:35]S(C(F)(F)F)(=O)=O)(=[O:34])=[O:33].[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:30][C:31]([F:44])([F:43])[S:32]([O-:35])(=[O:34])=[O:33].[CH2:8]([N+:15]12[CH2:28][CH:17]([CH2:16]1)[C:18]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[CH:19][CH2:20]2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 9912522(+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol

Product 1

HCID 102245361-Benzyl-4-(4-fluorophenyl)-l-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.5 ml) was added to a solution of (+)-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (2.82 g) in toluene (22.18 g) and the mixture was stirred at ambient temperature. The solution was cooled to 5° C. in an ice/water bath and the trifluoromethanesulphonic anhydride (1.8 ml) was added dropwise over 5 minutes. The mixture was stirred at 0° C. to room temperature for 4 hours, then stood for 48 hours. Water (25 ml) was added. The mixture was stirred for 2 minutes and then ethyl acetate and 4M-NaOH were added to dissolve an insoluble oil. The organic layer was separated, washed with water (25 ml), and then dried, filtered and evaporated to give 1-benzyl-4-(4-fluorophenyl)-1-azoniabicyclo[3.1.1]hept-3-ene trifluoro-methanesulphonate as an oil The oil was triturated with 60-80° C. petrol to give a solid.

Workup

  1. temperatureThe solution was cooled to 5° C. in an ice/water bath
  2. stirringThe mixture was stirred at 0° C. to room temperature for 4 hours
  3. stirringThe mixture was stirred for 2 minutes
  4. dissolutionto dissolve an insoluble oil
  5. customThe organic layer was separated
  6. washwashed with water (25 ml)
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-761603c3e8f148d09e7ed2aff1cf52ee
Source dataset
uspto-grants-2005_09
Patent number
US06949650B2

Reaction notes

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