2-Aminothiazole → 4-Cyclohexyl-4-(thiazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1795172Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795172
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([CH2:14][NH:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 21552-AminothiazoleHCID 5049666Sodium triacetoxyborohydrideHCID 219368754-Cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 210237784-Cyclohexyl-4-(thiazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Cyclohexyl-4-formyl-piperidine-1-carboxylic acid tert-butyl ester, 3, (296 mg, 1.0 mmol) and 2-aminothiazole (103 mg, 1.0 mmol) are dissolved in toluene (15 mL), and the mixture was refluxed using a Dean-Stark apparatus overnight. The solution is then cooled to room temperature and sodium triacetoxyborohydride added. The reaction is stirred at room temperature for three hours and then diluted with ethyl acetate. The reaction mixture is washed with aqueous sodium bicarbonate and brine. The solvent is removed under reduced pressure and the residue purified by preparative HPLC to afford 312 mg (82% yield) of the desired compound. MS (ESI) m/z 380 (M+H+)

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. customa Dean-Stark apparatus overnight
  3. washThe reaction mixture is washed with aqueous sodium bicarbonate and brine
  4. customThe solvent is removed under reduced pressure
  5. customthe residue purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-33eec37674764f2fa0152207c7eb01cc
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026335B2

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