Chloroacetaldehyde → Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

HRID 253982

Reaktionsgleichung

Reaktionsgleichung von HRID 253982
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[S:3])[NH2:2].Cl[CH2:18][CH:19]=O>CC(C)=O>[S:3]1[CH:19]=[CH:18][N:2]=[C:1]1[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Komponenten

4

Edukt 2

HCID 33Chloroacetaldehyde2×HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

Produkt 1

HCID 58179889Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-thiocarbamoylpiperidine-1-carboxylate (1 g, 4.09 mmol) in acetone (5 mL) was added 2-chloroacetaldehyde (0.32 g, 4.08 mmol). The mixture was heated under reflux for 4 hours. Additional 2-chloroacetaldehyde (0.32 g, 4.08 mmol) was added and heating was continued for another 14 hours. The solvent was removed by evaporation and the crude product was purified by silica gel chromatography to give tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate as an oil [530 mg (1.97 mmol); LC-MS=213.1 (M+H); 1H NMR (300 MHz, CDCl3) 7.74 (d, J=3.3 Hz, 1H), 7.26 (d, J=3.3 Hz, 1H), 4.23 (brd, 2H), 3.22 (m, 1H), 2.91 (t, 2H), 2.14 (m, 2H), 1.77 (m, 2H), 1.48 (s, 9H)].

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureheating
  4. customThe solvent was removed by evaporation
  5. customthe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-89ac6dc4724d42c688b61ccf506d6284
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872031B2

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