Reaktion #519208

ord-548f643ff66044e792b273f96dcde138

Reaktionsgleichung

COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1
1-(2-methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine
CC(C)[CH2][Al][CH2]C(C)C
Dibal-H
COc1ccccc1N1CCN(CCC(c2ccccc2)C(O)C2CCCCC2)CC1
1-(2-methoxyphenyl)-4-[4-(cyclohexyl)-4-(hydroxy)-3-(phenyl)butyl]piperazine
Ausbeute 101.8%

Lösungsmittel

Reaktionsbedingungen

Temperatur
-78°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturslowly warmed to room temperature for 16 hours
  2. 2
    SonstigeWorkup followed by purification by flash chromatography

Vorschrift

To a stirred solution of 1-(2-methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine (0.11 g, 0.20 mmol) in methylene chloride (10 mL) at −78° C. under nitrogen was added Dibal-H™ solution (0.89 mmol). The mixture was stirred at −78° C. for 1 hour and then slowly warmed to room temperature for 16 hours. Workup followed by purification by flash chromatography gave pure 1-(2-methoxyphenyl)-4-[4-(cyclohexyl)-4-(hydroxy)-3-(phenyl)butyl]piperazine (0.086 g) in 78% yield. The oxalate salt was prepared as described above.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06660859B2uspto-grants-2003_12