Triethylamine → Tert-butyl 3-(methylcarbamoyl)piperidine-1-carboxylate

HRID 1842331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842331
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](N1C=CN=C1)([N:19]1C=CN=C1)=O.C(N(CC)CC)C.Cl.CN>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[O:16])[NH:19][CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 6364545Methylamine hydrochloride

Produkt 1

HCID 18154653Tert-butyl 3-(methylcarbamoyl)piperidine-1-carboxylateAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Amine preparation: To a solution of 1-(tert-butoxycarbonyl)-3-piperidine-carboxylic acid (0.50 g) in DMF (3 mL) was added 1,1′-carbonyldiimidazole (0.70 g). The reaction mixture was stirred for 4 h and then triethylamine (0.60 mL) followed by methylamine hydrochloride (0.29 g) was added. After stirring for 24 h the reaction mixture was then diluted with ethyl acetate, washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 3-methylcarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (0.41 g). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.

Aufarbeitung

  1. additionwas added
  2. stirringAfter stirring for 24 h the reaction mixture
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4f4ccbce35fd4bb6bab5b6983525ecf6
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946217B2

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