Hydrochloric Acid → Tert-butyl 4-(3-oxo-4-phenylbutanoyl)piperidine-1-carboxylate

HRID 278195

Reaktionsgleichung

Reaktionsgleichung von HRID 278195
[H-].[Na+].[C:3]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].[C:19]1([CH2:25][C:26](OC)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C1COCC1.CCOCC>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][CH:6]([C:3](=[O:5])[CH2:4][C:26](=[O:27])[CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7559Methyl phenylacetateHCID 24758Sodium hydrideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 18187492Tert-butyl 4-(3-oxo-4-phenylbutanoyl)piperidine-1-carboxylateAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 60% sodium hydride (1.07 g) in THF (15 mL) at 0° C. was added a solution of 4-acetyl-1-(t-butoxycarbonyl)piperidine from Step B2 (3.03 g, 13.3 mmol) and methyl phenylacetate (6.01 g, 39.9 mmol) in THF (6 mL) over 20 min. The reaction was stirred for another 4 h as it was allowed to warm to rt. The mixture was diluted with ether (30 mL) and poured into 1N HCl. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic layers were washed with brine (150 mL), dried over sodium sulfate and concentrated. The crude product was purified by FC (20% ethyl acetate in hexanes) to give the title compound (3.02 g). Rf: 0.30 (20% ethyl acetate in hexane). The 1H NMR data was the same as that obtained from the product of Method A.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted three times with ether
  3. washThe combined organic layers were washed with brine (150 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by FC (20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9d295978d2a24b2185c41d4159e36016
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358979B1

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