Acetone → Cyclopropyl(4-(3-(4-((2r)-2-(isopropylamino)propanoyl)-1-piperazinyl)propoxy)phenyl)methanone

HRID 411255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411255
C([BH3-])#N.[Na+].[NH2:5][C@H:6]([CH3:30])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)=[O:8].[CH3:31][C:32]([CH3:34])=O>>[CH:27]1([C:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:11][CH2:10][N:9]([C:7](=[O:8])[C@H:6]([NH:5][CH:32]([CH3:34])[CH3:31])[CH3:30])[CH2:14][CH2:13]3)=[CH:24][CH:23]=2)=[O:26])[CH2:29][CH2:28]1

Komponenten

4

Edukt 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 9906860A 304121

Produkt 1

HCID 44304056Cyclopropyl(4-(3-(4-((2r)-2-(isopropylamino)propanoyl)-1-piperazinyl)propoxy)phenyl)methanoneAusbeute 25 %

Versuchsvorschrift

Sodium cyanoborohydride (75 mg, 1.2 mmol) was added to a room temperature solution of Example 138 (401 mg, 1 mmol) in acetone (10 mL). After stirring overnight, the reaction mixture was concentrated, and the concentrate was taken up in dichloromethane and washed with water, and brine, dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography using dichloromethane:methanol (9:1) as the eluant. The product was obtained in 25% yield.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. washwashed with water, and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography
  7. customThe product was obtained in 25% yield

Quellen und Nachweise

ORD-Eintrag
ord-d6ad7b7576454d32909299eead388320
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559140B2

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