Methanol → N-Allyl-N,N-di-n-octylamine

Participants

Reaction Steps

Resin 3 (0.42 mmol g−1 (est.), 160 mg) in DMF (2 cm3) was treated with dioctylamine (1.7 mmol, 515 mm3) at 20° C. for 24 h. The resin was washed with DMF (10×5 cm3) and DCM (10 cm3), resuspended in DMF (2 cm3) and treated with allyl bromide (4.25 mmol, 365 mm3) at 20° C. for 24 h. The solvent and the reagent was then removed by filtration and the resin washed with DCM (2×20 cm3). The elimination was performed in DCM (4 cm3) with DIPEA (1.72 mmol, 300 mm3) over night. The filtrate of this last reaction step was combined with the DCM and MeOH wash (25 cm3) from the resin and evaporated. It gave 14 contaminated with DIPEA in 38 mg yield. The amine was transferred in little DCM (<0.5 cm3) to a K2CO3 covered dry silica column (5 g). Impurities were washed away with hexane and the amine eluted with ethyl acetate. After the removal of the solvent 14 (0.043 mmol, 12 mg, 64%) was obtained as a colourless oil. It was contaminated with 5% of 4 of a previous cycle.

Provenance & Evidence