Réaction #1466692

Équation de réaction

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

potassium carbonate

2-chloro-4-fluoro benzothiazole

dimethylformamide

→

title compound

Rendement 58.0%

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

Rendement 58.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autrefitted with a reflux condenser
2. 2
   Températurethe stirred mixture was heated at 60°, under nitrogen, for 48 h
3. 3
   TempératureThe mixture was cooled
4. 4
   Lavagewashed with brine (2×25 mL)
5. 5
   SéchageThe combined organic extracts were dried over sodium sulfate
6. 6
   Concentrationconcentrated
7. 7
   Autrepurified by silica gel chromatography (80% ethyl acetate/hexanes eluent)

Mode opératoire

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-mercapto-10b-methyl-1,2,3,4,4a,-5,6,10b-octahydrobenzo[f]quinolin-3-one (100 mg, 0.38 mmol), potassium carbonate (158 mg, 1.14 mmol), 2-chloro-4-fluoro benzothiazole (86 mg, 0.46 mmol and 1 mL of anhydrous dimethylformamide, fitted with a reflux condenser, and the stirred mixture was heated at 60°, under nitrogen, for 48 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (80% ethyl acetate/hexanes eluent) to give 91 mg (58%) of the title compound as an amorphous solid. mp 140°-145°. FDMS: m/e=412. α[D]589 =+70.06 (c=0.52, chloroform).

Source