Sesamol → (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-1-benzyl-4-(4-fluorophenyl)piperidine

HRID 431265Notes

Reaction equation

HRID 431265 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C@H:10]([CH2:21][O:22]S(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]1[O:31][C:30]2[CH:32]=[C:33](O)[CH:34]=[CH:35][C:29]=2[O:28]1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C@H:10]([CH2:21][O:22][C:33]2[CH:34]=[CH:35][C:29]3[O:28][CH2:27][O:31][C:30]=3[CH:32]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 68289SesamolHCID 23665647Potassium tert-butoxideHCID 88118315(+)-cis-1-Benzyl-4-(4-fluorophenyl)-3-mesyloxymethylpiperidine

Product 1

HCID 9953865(3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-1-benzyl-4-(4-fluorophenyl)piperidineYield 64%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution containing 7.54 g (0.02 mol) of (+)-cis-1-benzyl-4-(4-fluorophenyl)-3-mesyloxymethylpiperidine in 120 ml of tertiary butanol, 3 g (0.022 mol) of sesamol and 3.35 g (0.03 mol) of potassium tertiary butoxide are added and the mixture is boiled under reflux for 12 hours. After completion of the reaction the mixture is evaporated and 100 ml of dichloromethane and 50 ml of water are added to the residue. After separation, the organic phase is washed with water until neutral, dried over a drying agent and after filtration the filtrate is evaporated to solvent-free. The evaporation residue is recrystallized from 25 ml of isopropanol. The precipitated product is filtered at 0° C. to obtain 5.37 g (64%) of title compound, m.p.: 98-100° C.; [α]D20−37.1° (c=1, chloroform).

Workup

  1. additionare added
  2. temperatureunder reflux for 12 hours
  3. customAfter completion of the reaction the mixture
  4. customis evaporated
  5. addition100 ml of dichloromethane and 50 ml of water are added to the residue
  6. customAfter separation
  7. washthe organic phase is washed with water until neutral,
  8. customdried over a drying agent
  9. filtrationafter filtration the filtrate
  10. customis evaporated to solvent-free
  11. customThe evaporation residue is recrystallized from 25 ml of isopropanol
  12. filtrationThe precipitated product is filtered at 0° C.

Sources & evidence

ORD record
ord-ace9bde5259f4cc1b3054d496bfb94b0
Source dataset
uspto-grants-2003_12
Patent number
US06657062B1

Reaction notes

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