Methanol → tert-Butyl 2-(2-(6-(methylsulfonamido)-4-oxospiro[chroman-2,4'-piperidine]-1'-yl)ethoxy)ethylcarbamate

Participants

Reaction Steps

A solution of N,N-diisopropylethylamine (1.3 mL, 7.5 mmol), tert-butyl 2-(2-bromoethoxy)ethyl-carbamate (4, 0.59 g, 2.2 mmol), and N-(4-oxospiro[chroman-2,4′-piperidine]-6-yl)methanesulfon-amide hydrochloride (11, 0.5 g, 1.4 mmol) in 10 mL of anhydrous DMF was stirred at 60-65° C. After ˜24 hours TLC (silica gel, 10% methanol in dichloromethane, UV visualization) showed almost complete disappearance of starting amine 11 (Rf=0.02−0.06) and appearance of one major new product (Rf=0.35-0.45). The reaction was allowed to cool to room temperature and 10 mL of water was added. The resulting mixture was transferred to a separatory funnel with the aid of ethyl acetate and the layers were separated. The aqueous layer was extracted with 20 mL of ethyl acetate. The organic extracts were combined, washed successively with 10 mL portions of water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure on a rotary evaporator followed by high vacuum to provide 0.94 g of orange-brown oil.

Provenance & Evidence