Triethylamine → 4-hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

HRID 489615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489615
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5].Cl.C(N(CC)CC)C.[CH2:21]([O:28][C:29](ON1C(=O)CCC1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.O.C(OCC)(=O)C>[CH2:2]([O:3][C:4]([C:6]1[CH2:7][N:8]([C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:30])[CH2:9][CH2:10][C:11]=1[OH:12])=[O:5])[CH3:1]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 690289334-hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl esterAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-piperidone-3-carboxylate hydrochloride (5 g, 24.05 mmol) in THF (70 mL) and water (35 mL) at 0° C., was added triethylamine (8.7 mL, 62.5 mmol), followed by N-(benzyloxycarbonyloxy)succinimide (7.79 g, 31.27 mmol). The reaction mixture was stirred and allowed to warm to room temperature. After 3 hours the reaction mixture was diluted with water (50 mL) and ethyl acetate (100 mL) added. The aqueous phase was extracted into ethyl acetate (2×100 mL). The organic phases were combined, washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent, ethyl acetate:pentane=1:5) to give 4-hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester as a colorless oil (7.26 g, 94%). MS (EI) 305 (M+).

Aufarbeitung

  1. additionadded
  2. extractionThe aqueous phase was extracted into ethyl acetate (2×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe crude product was purified by column chromatography on silica gel (eluent, ethyl acetate:pentane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-a0a612587fba4b9491829a44f295bef0
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977263B2

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