Reaktion #164592

Reaktionsgleichung

Intermediate 33A

2-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one

3-quinuclidinol

triphenylphosphine

diisopropyl azodicarboxylate

2-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one

→

2-(3-chlorophenyl)-3-methyl-6-(quinuclidin-3-yloxy)quinazolin-4(3H)-one

Ausbeute 12.9%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was purified by scx cartridge (1 g)

Vorschrift

To a solution of 2-(3-chlorophenyl)-6-hydroxy-3-methylquinazolin-4(3H)-one (Intermediate 33A) (100 mg, 0.35 mmol), 3-quinuclidinol (44 mg, 0.35 mmol) and triphenylphosphine (137 mg, 0.35 mmol) in tetrahydrofuran (2 mL) was added dropwise diisopropyl azodicarboxylate (0.103 mL, 0.52 mmol). The reaction was stirred for 20 h. The mixture was purified by scx cartridge (1 g) followed by acidic prep hplc then scx (500 mg) to afford 2-(3-chlorophenyl)-3-methyl-6-(quinuclidin-3-yloxy)quinazolin-4(3H)-one (18 mg, 0.045 mmol).

Quelle