Potassium Carbonate → tert-butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylate

HRID 1162331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162331
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1[NH:17][C:18]([CH3:23])=[C:19]([CH:21]=O)[N:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.C(O)(=O)C>[CH3:15][C:16]1[NH:17][C:18]([CH3:23])=[C:19]([CH2:21][NH:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[N:20]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 132064322,5-Dimethyl-1H-imidazole-4-carbaldehyde

Produkt 1

HCID 23138170tert-butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylateAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

N-(tert-butoxycarbonyl-4-piperidinyl)amine (4.8 g), 2,5-dimethylimidazole-4-carbaldehyde (3.0 g) and acetic acid (1.7 ml) were dissolved in 1,2-dichloroethane (50 ml), under ice-cooling, sodium triacetoxyborohydride (7.7 g) was added thereto, and mixed at room temperature for 15 hours. The reaction solution was poured into an aqueous potassium carbonate solution, and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and then the residue was purified with silica gel column to obtain a pale yellow oily title compound (8.0 g, quantitative).

Aufarbeitung

  1. temperaturecooling
  2. additionmixed at room temperature for 15 hours
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified with silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-129d51e43502499fab431054ed92145d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820673B2

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