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

HRID 1689905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689905
[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-55bb470e73f64edcbc77102906cd6cae
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153629B2

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