Diisopropylethylamine → Ethylbis(propan-2-yl)amine hydrochloride

Participants

Reaction Steps

344 mg (0.5 mmole) of N6 -benzoyl-5'-O-dimethoxy-trityl-2'-O-methyl-adenosine (compound IIa) were dissolved in 2 ml of anhydrous THF, and the resulting solution was admixed with 362 μl (2 mmoles) of diisopropyl ethyl amine (DIPEA) with stirring under an argon atmosphere at room temperature. Then 300 μl (1.5 mmoles) of N,N-diisopropyl-amino-methoxy-chlorophosphine was added over 1 minute. After 5 minutes, DIPEA hydrochloride was formed as a white precipitate. Stirring was continued at room temperature and, after 45 minutes, the reaction mixture was analysed by a chromatography using silica gel 60 TLC (the mobile phase: n-hexane/acetone (1:1) containing 5% of triethyl amine) to confirm whether the spot of the starting material (Rf =0.52) had disappeared and the spot of the product (IIb2) (Rf =0.76) had appeared. After the confirmation of the latter spot, 20 ml of ethyl acetate was added to the reaction mixture under cooling with ice. Then the reaction mixture was washed twice with 15 ml of an ice-cooled saturated aqueous sodium bicarbonate solution, and then washed once with 15 ml of an ice-cooled saturated aqueous sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate. After the sodium sulfate had been separated by a filtration, the filtrate was evaporated to dryness. The oily residue thus obtained was dried under reduced pressure, and dissolved in 2 ml of dichloromethane, and added dropwise with stirring to 200 ml of n-hexane which had been cooled to a temperature of -50° C., whereby a white precipitate was formed

Provenance & Evidence