Sodium cyanoborohydride → 7-chloro-3-(3,5-dimethylphenyl)-4-{1-[4-(4-methoxyphenyl)-butyl]-piperidin-2-yl-methoxy}-1H-quinolin-2-one

HRID 1857605

Reaktionsgleichung

Reaktionsgleichung von HRID 1857605
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][NH:24]3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][CH:40]=O)=[CH:33][CH:32]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:21][CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][N:24]3[CH2:40][CH2:39][CH2:38][CH2:37][C:34]3[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:36][CH:35]=3)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 104875554-(4-Methoxyphenyl)butanalHCID 221300057-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one

Produkt 1

HCID 540325717-chloro-3-(3,5-dimethylphenyl)-4-{1-[4-(4-methoxyphenyl)-butyl]-piperidin-2-yl-methoxy}-1H-quinolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-(piperidin-2-yl-methoxy)-1H-quinolin-2-one (prepared essentially as described in Example 10, 34 mg in 3.0 mL dry methanol) was added 18 mg of 4-(4-methoxyphenyl)-butyraldehyde, 150 mg powdered 4 Å molecular sieves and one drop of acetic acid. After 30 minutes, 0.13 mL of a 1M solution of sodium cyanoborohydride in tetrahydrofuran was added and the mixture stirred at room temperature for 18 hours. At this time the reaction mixture was filtered through diatomaceous earth and the filtrate concentrated in vacuo. Purification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3) gave the title compound, 39 mg.

Aufarbeitung

  1. filtrationAt this time the reaction mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by flash chromatography on silica gel (chloroform:methanolic ammonium hydroxide, 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-4b565d37fcf64e1fbf76b1d070a774de
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147088

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