Propane sultone → 3-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonic acid

HRID 242087

Reaktionsgleichung

Reaktionsgleichung von HRID 242087
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25]1[CH2:31][S:28](=[O:30])(=[O:29])[O:27][CH2:26]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:26][CH2:25][CH2:31][S:28]([OH:30])(=[O:29])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 14264Propane sultoneHCID 24758Sodium hydrideHCID 582462431-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

Produkt 1

HCID 582463633-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The crude 1-[1-(4-chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol (3.5 g, 11.22 mmol) was added to a suspension of sodium hydride (60% in mineral oil, 471 mg, 11.79 mmol) in dimethylformamide (25 mL). After stirring for 30 min at room temperature 1,3-propanesultone (1.44 g, 11.79 mmol) was added dropwise. The reaction mixture was stirred over night at room temperature. The dimethylformamide was removed in vacuo. The crude product (8.4 g) was used for the next step without further purification.

Aufarbeitung

  1. additionwas added dropwise
  2. customThe dimethylformamide was removed in vacuo
  3. customThe crude product (8.4 g) was used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d107030a440a4fcdaa364814be7bf77a
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653100B2

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