Water → (+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol

HRID 497921Notes

Reaction equation

HRID 497921 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[K+].FC(F)(F)S([O-])(=O)=O.[CH2:14]([N+:21]12CC([CH2:26]1)[C:24]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[CH:23][CH2:22]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[Na+]>C1(C)C=CC=CC=1.CC(O)C>[CH2:14]([N:21]1[CH2:22][CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH:2]([CH2:1][OH:4])[CH2:26]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 517044Potassium AcetateHCID 102245361-Benzyl-4-(4-fluorophenyl)-l-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate

Product 1

HCID 9912522(+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent4×HCID 3776IsopropanolSolvent2×

Procedure

Potassium acetate (0.14 g) was added to a stirred solution of 1-benzyl-4-(4-fluorophenyl)-1-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate (0.5 g) in toluene (2.5 ml) and propan-2-ol (2.5 ml). The mixture was then boiled and stirred under reflux for 24 hours. The mixture was cooled to room temperature and toluene (10 ml) and water (5 ml) were added. The organic layer was separated, dried and evaporated to leave an oil. A solution of the oil in propan-2-ol (2 ml) and toluene (2 ml) was treated with 4M-NaOH (0.4 ml). The mixture was boiled under reflux for 2 hours then cooled to room temperature. Water (5 ml) and toluene 95 ml) were added. The organic layer was separated, washed with water (2×5 ml) and evaporated to give (+,−)-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (ee 5.48%).

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customto leave an oil
  6. temperatureunder reflux for 2 hours
  7. temperaturethen cooled to room temperature
  8. customThe organic layer was separated
  9. washwashed with water (2×5 ml)
  10. customevaporated

Sources & evidence

ORD record
ord-1026a31f2d754856a47802297b409b3e
Source dataset
uspto-grants-2005_09
Patent number
US06949650B2

Reaction notes

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