Sodium hydride → 4-[2-(4-Methoxy-benzyl)-1-oxo-7-phenyl-1,2-dihydro-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1930224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930224
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24](=[O:34])[N:23]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)[CH:22]=[CH:21]2>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:24](=[O:34])[N:23]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)[CH:22]=[CH:21]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 576525476-Fluoro-2-[(4-methoxyphenyl)methyl]-7-phenylisoquinolin-1(2H)-one

Produkt 1

HCID 576525764-[2-(4-Methoxy-benzyl)-1-oxo-7-phenyl-1,2-dihydro-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

168 mg (0.83 mmol) 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester were dissolved in 5 mL of dimethylacetamide and 20 mg (0.83 mmol) of sodium hydride (60%) were added. The mixture was stirred at room temperature. After 30 minutes a solution of 240 mg (0.67 mmol) 6-fluoro-2-(4-methoxy-benzyl)-7-phenyl-2H-iso-quinolin-1-one (315) in 5 mL of dimethylacetamide was added and stirring was continued at room temperature. After standing overnight, 20 mg (0.83 mmol) of sodium hydride (60%) were added and the solution was stirred at 100° C. After 1 h, the solvent was removed i. vac. and saturated sodium bicarbonate solution was added. The aqueous phase was extracted three times with dichloromethane. The organic layers were dried with MgSO4 and evaporated. The crude product was purified by preparative HPLC. Rt=1.98 min (Method C). Detected mass: 541.7 (M+H+).

Aufarbeitung

  1. stirringstirring
  2. customwas continued at room temperature
  3. stirringthe solution was stirred at 100° C
  4. waitAfter 1 h
  5. customthe solvent was removed i
  6. additionand saturated sodium bicarbonate solution was added
  7. extractionThe aqueous phase was extracted three times with dichloromethane
  8. dry with materialThe organic layers were dried with MgSO4
  9. customevaporated
  10. customThe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-42d6b429e4c94eb48daf99b78af0fd48
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188117B2

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