Trimethylsilyl triflate → [1-(6-Chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]acetic acid methyl ester

HRID 420580Notes

Reaction equation

HRID 420580 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7](=[O:25])[CH:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(=O)([O-])O.[Na+]>O1CCCC1.[Cu](I)I>[CH3:5][O:6][C:7](=[O:25])[CH2:8][C:9]1([CH2:1][CH3:2])[CH2:10][CH2:11][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 57966063[1-(6-Chlorobenzothiazole-2-yl)piperidine-4-ylidene]acetic acid methyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 57966339[1-(6-Chlorobenzothiazole-2-yl)-4-ethyl piperidine-4-yl]acetic acid methyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-25 °C

Procedure

Copper iodide (1.77 g) was suspended in tetrahydrofuran (18 mL), and ethyl magnesium bromide (1.0 M tetrahydrofuran solution, 18.6 mL) was added thereto at −30° C. After stirring at −25° C. for 0.5 hour, the reaction solution was cooled to −78° C. To the mixture was added dropwise a solution of [1-(6-chlorobenzothiazole-2-yl)piperidine-4-ylidene]acetic acid methyl ester (1.00 g) in tetrahydrofuran (10 mL), and then added trimethylsilyl trifluoromethansulfonate (1.12 mL). After stirring at −78° C. for 2 hours, aqueous sodium hydrogencarbonate solution was added thereto. After filtration of the insoluble material, the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (979 mg). Yield: 90%.

Workup

  1. customat −30° C
  2. temperaturethe reaction solution was cooled to −78° C
  3. stirringAfter stirring at −78° C. for 2 hours
  4. filtrationAfter filtration of the insoluble material
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-30a6ad990ee24aa59a674372ae6eb9c0
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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