Water → (+/-)-1-Methyl-3-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-piperidin-2-one

HRID 230259

Reaktionsgleichung

Reaktionsgleichung von HRID 230259
CO[C:3](=[O:26])[CH:4]([C:9]1[N:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[N:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)[CH2:5][CH2:6][CH:7]=O.[CH3:27][NH2:28].[BH4-].[Na+].O>CO.CO.CCOC(C)=O>[CH3:27][N:28]1[CH2:7][CH2:6][CH2:5][CH:4]([C:9]2[N:13]3[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]3=[N:11][C:10]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:3]1=[O:26]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 587635832-(6-Methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester

Produkt 1

HCID 11325081(+/-)-1-Methyl-3-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-piperidin-2-oneAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of (+/−)-2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-5-oxo-pentanoic acid methyl ester 35c (0.085 g, 0.253 mmol) in methanol (1 mL) at room temperature under Ar atmosphere was added a 40% aqueous solution of methyl amine (MeNH2) (0.021 mL, 0.253 mmol). The reaction mixture was stirred for 1 h at room temperature. NaBH4 (0.019 g, 0.506 mmol) was added at room temperature. After 30 min, water (30 mL) was added, and the aqueous phase was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), and concentrated in vacuo to the crude product. The pure product was obtained by column chromatography over silica gel (EtOAc, then 4:96 MeOH/EtOAc as eluent) which gave the title compound (0.03 g, 31%) as a white solid. The combined organic layers were washed with water, dried (MgSO4), and concentrated in vacuo to the crude product. 1H NMR (400 MHz, CDCl3) δ 1.99 (m, 3H), 2.11 (m, 1H), 2.31 (s, 3H), 2.38 (s, 3H), 3.05 (s, 3H), 3.41 (m, 1H), 3.53 (m, 1H), 4.25 (m, 1H), 6.99 (d, J=9.1 Hz, 1H), 7.22 (m, 3H), 7.46 (s, 1H), 7.53 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 18.9, 21.5, 23.1, 26.1, 35.4, 39.7, 50.3, 117.4, 119.1, 121.5, 121.7, 127.0, 129.1, 129.3, 132.4, 137.5, 143.9, 144.4, 168.7. Mass spectrum m/e 335 (M+).

Aufarbeitung

  1. waitAfter 30 min
  2. extractionthe aqueous phase was extracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo to the crude product
  5. customThe pure product was obtained by column chromatography over silica gel (EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-69a491a78ccc49ef84bbb71870cbf487
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566725B2

Verknüpfte Notizen

Wird geladen…