2-Cyanoethyl tetraisopropylphosphorodiamidite → Diisopropylamino-5-(carbomethoxy)pentyloxy-2-cyanoethoxy phosphine

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.786 g (5.37 mmole) of methyl-6-hydroxyhexanoate and 0.48 g (2.8 mmole) of diisopropylammonium tetrazolide in 25 ml of dichloromethane were added dropwise 1.62 g (5.37 mmole) of bis(diisopropyl amino)-2-cyanoethyoxyphosphine (Aldrich). The resulting solution was stirred at 25° C. for 2 hours and extracted with phosphate buffer at pH 7. Drying over magnesium sulfate and fast chromatography on silica gel (40% ethylacetate-hexanes, trace triethylamine) yielded the diisopropylamino-5-(carbomethoxy)pentyloxy-2-cyanoethoxy phosphine linking group as a colorless oil (1.30 g: 70%).

Provenance & Evidence