Potassium ethoxide → 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester

HRID 1711220

Reaktionsgleichung

Reaktionsgleichung von HRID 1711220
[CH2:1]([O:3][C:4](=[O:23])[C:5](=[O:22])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:8]=1[N+:19]([O-:21])=[O:20])[CH3:2].[O-]CC.[K+].[C:28]([O:33][CH2:34][CH2:35]Br)(=[O:32])[C:29]([CH3:31])=[O:30]>C1COCC1.O.CCOCC>[CH2:1]([O:3][C:4](=[O:23])[C:5](=[O:22])[CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:8]=1[N+:19]([O-:21])=[O:20])[CH2:31][C:29](=[O:30])[C:28]([O:33][CH2:34][CH3:35])=[O:32])[CH3:2]

Komponenten

7

Edukt 3

HCID 23670592Potassium ethoxideHCID 597967713-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl esterHCID 86587973Bromoethyl pyruvate

Produkt 1

HCID 597967863-(2-Nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid di ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-(2-nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester (ii) in THF is treated with potassium ethoxide (“KOEt”) (1 eq), followed by bromoethyl pyruvate (1.05 eq), at 0° C. The reaction is allowed to warm to room temperature over 90 min. The reaction is diluted with water and ether, partitioned, and the aqueous layer is washed with ether. The combined organic layers are dried over MgSO4, filtered and concentrated. Chromatography gives 3-(2-nitro-3-piperidin-1-yl-phenyl)-2,5-dioxo-hexanedioic acid diethyl ester (iii).

Aufarbeitung

  1. custompartitioned
  2. washthe aqueous layer is washed with ether
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7a09d29648ba441496f25efeae018233
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790724B2

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