Reaktion #1466736

Reaktionsgleichung

(+)-(4aR)-(10bR)-4-methyl-8-(3-aminophenyl)-10b-methyl 1,2,3,4,4a,-5,6,10b octahydrobenzo[f]quinolin-3-one

pyridine

dichloromethane

pivaloyl chloride

→

title compound

Ausbeute 64.0%

(+)-(4aR)-(10bR)-4-methyl-8-(3-[pivaloylamino]phenyl)-10methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Ausbeute 64.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to 0°
2. 2
   Waschenwashed with 5% aqueous hydrochloric acid solution, water, 5% aqueous sodium hydroxide solution, water
3. 3
   Trocknenthe combined organic extracts were dried over sodium sulfate
4. 4
   Einengenconcentrated
5. 5
   Sonstigechromatographed on silica gel (ethyl acetate eluent)

Vorschrift

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-(3-aminophenyl)-10b-methyl 1,2,3,4,4a,-5,6,10b octahydrobenzo[f]quinolin-3-one (31 mg, 0.097 mmol), N,N-dimethylaminopyridine (3 mg, 0.024 mmol), 1 mL of pyridine and 0.5 mL of dichloromethane. The solution was cooled to 0°, and excess pivaloyl chloride (0.086 mL, 0.69 mmol) was added. The stirred mixture was allowed to warm to room temperature over 2 h. The mixture was diluted with chloroform, and washed with 5% aqueous hydrochloric acid solution, water, 5% aqueous sodium hydroxide solution, water, and the combined organic extracts were dried over sodium sulfate, concentrated and chromatographed on silica gel (ethyl acetate eluent) to give 25 mg (64%) of the title compound as a yellow solid. mp 95°-98°. FDMS m/e=404. α[D]589 =+62.50 (c=0.16, chloroform).

Quelle