Methyl vinyl sulfone → tert-butyl 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-[2-(methylsulfonyl)ethoxy]piperidine-1-carboxylate

HRID 44729

Reaktionsgleichung

Reaktionsgleichung von HRID 44729
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2([OH:32])[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].[H-].[Na+].[CH:35]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH2:36]>O1CCCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][C:19]2([O:32][CH2:36][CH2:35][S:37]([CH3:40])(=[O:39])=[O:38])[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 57515386tert-butyl 4-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 57515407tert-butyl 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-[2-(methylsulfonyl)ethoxy]piperidine-1-carboxylateAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-hydroxypiperidine-1-carboxylate (prepared as described in Part E of Example 4, 1.9 g, 4.3 mmol) in tetrahydrofuran (17 mL) at rt was added solid NaH (60%, 17 mg, 0.43 mmol). After 10 min, methyl vinyl sulfone (0.92 g, 8.6 mmol) was added dropwise. After 1 h, the reaction was quenched with water (50 mL) and extracted with ethyl acetate (50 mL). The organic layer was concentrated under reduced pressure to afford a yellow oil. Purification by flash chromatography (silica gel, eluted with 5% methanol/dichloromethane) yielded tert-butyl 4-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-[2-(methylsulfonyl)ethoxy]piperidine-1-carboxylate (0.40 g, 19%).

Aufarbeitung

  1. waitAfter 1 h
  2. customthe reaction was quenched with water (50 mL)
  3. extractionextracted with ethyl acetate (50 mL)
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customto afford a yellow oil
  6. customPurification
  7. washby flash chromatography (silica gel, eluted with 5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d58df8470bba416480517be72f802634
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541438B2

Verknüpfte Notizen

Wird geladen…