Isoquinoline, 1-chloro- → [1-(1-Isoquinolyl)-4-piperidyl]methanol

HRID 1350563

Reaktionsgleichung

Reaktionsgleichung von HRID 1350563
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:2]1([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 140539Isoquinoline, 1-chloro-HCID 4207714-PiperidinemethanolHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 21096912[1-(1-Isoquinolyl)-4-piperidyl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

The process is performed as described in Example 2 (step 2.1). Starting with 2.50 g (15.28 mmol) of 1-chloroisoquinoline, 1.94 g (136.6 mmol) of 4-piperidylmethanol, 3.53 g (36.67 mmol) of sodium tert-butoxide, 0.285 g (0.46 mmol) of BINAP and 0.140 g (0.15 mmol) of tris(dibenzylideneacetone)dipalladium, and after chromatography on silica gel, eluting with a 98/2/0.2 and then 95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, 2.40 g of pure product are obtained in the form of a viscous orange oil.

Aufarbeitung

  1. washafter chromatography on silica gel, eluting with a 98/2/0.2
  2. addition95/5/0.5 mixture of dichloromethane, methanol and 28% aqueous ammonia, 2.40 g of pure product
  3. customare obtained in the form of a viscous orange oil

Quellen und Nachweise

ORD-Eintrag
ord-136a0284ad3f4342a7a808a2464547ee
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214798B2

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