tert-Butyl 4-sulfanylpiperidine-1-carboxylate → 4-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 221372

Reaktionsgleichung

Reaktionsgleichung von HRID 221372
CC([O-])(C)C.[K+].[N:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([CH2:18]OS(C)(=O)=O)[O:15][N:14]=2)=[CH:9][CH:8]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([SH:37])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>C1COCC1.CCOCC>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([S:37][CH2:18][C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:9]=[CH:8][N:7]=[CH:12][CH:11]=3)[N:17]=2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Komponenten

6

Edukt 3

HCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 57954388Methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester

Produkt 1

HCID 579544094-(3-Pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

t-BuOK (92 mg, 823 μmol) and methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester (Preparation 12, 150 mg, 588 μmol) were added to a stirred solution of 4-mercaptopiperidine-1-carboxylic acid tert-butyl ester (191 mg, 881 mol) in anhydrous THF (10 ml). After 100 min, the reaction mixture was diluted with Et2O, before being washed with NaHCO3 and brine. The organic layer was dried (MgSO4), filtered, and concentrated, then the residue was purified by column chromatography (IH-EtOAc, 3:2) to afford the title compound: RT=3.77 min; m/z (ES+)=377.2 [M+H]+.

Aufarbeitung

  1. washbefore being washed with NaHCO3 and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (IH-EtOAc, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-bad805c3d4a949ff81a3f21fa38fd134
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207147B2

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