Triethylamine → HCID 90449543, compound

Participants

Reaction Steps

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-hydroxybutyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (120.7 mg, 0.246 mmol) was dissolved in tetrahydrofuran (2.5 mL). Thereafter, triethylamine (46 μL, 0.32 mmol) and methanesulfonyl chloride (21 μL, 0.27 mmol) were added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 1 hour. Thereafter, insoluble matters were filtered, and the filtrate was then concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (2.4 mL), and S-potassium thioacetate (62 mg, 0.54 mmol) was then added to the above solution. The thus obtained mixture was stirred at room temperature for 15 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with water and brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=5:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(4-(acetylthio)butyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (89.2 mg, 66%) in the form of a brown oily product.

Provenance & Evidence