Reaktion #65920

Reaktionsgleichung

sodium hydroxide

2-cycloheptylcarbamoylmethylfluorene

methanol

hydrochloric acid

→

2-cycloheptylaminoethylfluorene

Ausbeute 66.0%

Lösungsmittel

chloroform

tetrahydrofuran

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONfollowed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-
2. 2
   Temperaturcooling
3. 3
   workup.ADDITIONwas added with ice-
4. 4
   Temperaturcooling
5. 5
   Temperaturcooling
6. 6
   TemperaturThe mixture was refluxed again for 30 minutes
7. 7
   TemperaturThe reaction mixture was then cooled with ice
8. 8
   Filtrationthe resulting solid was recovered by filtration
9. 9
   Waschenwashed with ether
10. 10
    SonstigeThe solid matter thus obtained
11. 11
    Sonstigedried
12. 12
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

In dry tetrahydrofuran (30 ml) was dissolved 2-cycloheptylcarbamoylmethylfluorene (1.9 g) followed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-cooling. The mixture was then refluxed for 4 hrs, at the end of which time methanol (0.72 ml) was added with ice-cooling. The mixture was stirred at room temperature for 30 minutes, followed by addition of concentrated hydrochloric acid (1.8 ml) with ice-cooling. The mixture was refluxed again for 30 minutes. The reaction mixture was then cooled with ice and the resulting solid was recovered by filtration and washed with ether. The solid matter thus obtained was dissolved in chloroform and the solution was alkalinized with aqueous sodium hydroxide solution. The chloroform layer was taken and dried and the solvent was distilled off under reduced pressure to give 2-cycloheptylaminoethylfluorene (1.2 g).

Quelle