Potassium Carbonate → tert-Butyl 3-(4-bromophenylthio)piperidine-1-carboxylate

HRID 78730

Reaktionsgleichung

Reaktionsgleichung von HRID 78730
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.CS(O[CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:18]2[CH2:19][CH2:14][CH2:15][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 568122N-Boc-3-mesyloxypiperidine

Produkt 1

HCID 86682785tert-Butyl 3-(4-bromophenylthio)piperidine-1-carboxylateAusbeute 18,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-bromobenzenethiol (4.697 g, 24.84 mmol), tert-butyl 3-methylsulfonyloxypiperidine-1-carboxylate (6.939 g, 24.84 mmol) and K2CO3 (6.866 g, 49.68 mmol) in DMF (40 mL) were stirred at ambient temperature for 16 hours. The reaction mixture was cooled to 0° C. and diluted with water. The reaction mixture was extracted with ethylacetate (×2) and the combined organic extracts washed with saturated aqueous sodium thiosulphate solution (×2), water (×2), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 330 g eluting with 0 to 50% Et2O/Petroleum Ether, loaded in DCM) to give tert-butyl 3-((4-bromophenyl)thio)piperidine-1-carboxylate as a colourless oil (1.68 g, 18% Yield). H NMR (400.0 MHz, CDCl3) δ 0.97-0.86 (m, 2H), 1.44 (s, 9H), 1.80-1.76 (m, 1H), 2.12-2.08 (m, 1H), 2.92-2.86 (m, 1H), 3.14-3.08 (m, 2H), 3.89 (br d, 1H), 4.05 (br s, 1H), 7.30 (d, 2H) and 7.45-7.43 (m, 2H) ppm;

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionThe reaction mixture was extracted with ethylacetate (×2)
  3. washthe combined organic extracts washed with saturated aqueous sodium thiosulphate solution (×2), water (×2)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (ISCO Companion, 330 g eluting with 0 to 50% Et2O/Petroleum Ether, loaded in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-be15b7c7894e4bedbaa71244c6cbea71
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841449B2

Verknüpfte Notizen

Wird geladen…