Trifluoroacetic acid → 2-[1-(3,5-Dichloro-2-hydroxy-benzyl)-4-fluoro-piperidin-4-ylmethyl]-isoindole-1,3-dione

HRID 2112555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2112555
FC(F)(F)C(O)=O.[F:8][C:9]1([CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Cl:27][C:28]1[C:29]([OH:37])=[C:30]([CH:33]=[C:34]([Cl:36])[CH:35]=1)[CH:31]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.C(N(CC)CC)C>[Cl:27][C:28]1[C:29]([OH:37])=[C:30]([CH:33]=[C:34]([Cl:36])[CH:35]=1)[CH2:31][N:12]1[CH2:13][CH2:14][C:9]([CH2:15][N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])([F:8])[CH2:10][CH2:11]1

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 666603,5-DichlorosalicylaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 230692652-(4-Fluoro-piperidin-4-ylmethyl)-isoindole-1,3-dione

Produkt 1

HCID 690694182-[1-(3,5-Dichloro-2-hydroxy-benzyl)-4-fluoro-piperidin-4-ylmethyl]-isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Triethylamine (9 ml) was added to a solution of a trifluoroacetic acid salt of 2-(4-fluoro-piperidin-4-ylmethyl)-isoindole-1,3-dione (22.6 g) in dichloromethane (300 ml). The obtained solution was stirred for 5 minutes, and then 3,5-dichloro-2-hydroxy-benzaldehyde (12.4 g) and NaBH(OAc)3 (19 g) were added and the mixture was stirred at room temperature for 3 hours. The obtained solution was washed with a saturated aqueous solution of sodium hydrogen carbonate, the dichloromethane was concentrated out, and the residue was recrystallized from ether to obtain 2-[1-(3,5-dichloro-2-hydroxy-benzyl)-4-fluoro-piperidin-4-ylmethyl]-isoindole-1,3-dione.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. washThe obtained solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. concentrationthe dichloromethane was concentrated out
  4. customthe residue was recrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-e747460c30224306a3b770e9b5f6af66
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07524841B2

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