N-octyloctan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The resin was washed with DMF (10×5 cm3) and DCM (10 cm3) The solvent and the reagent was then removed by filtration the resin washed with DCM (2×20 cm3) The filtrate of this last reaction step wash (25 cm3) from the resin evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In Examples 2, 3 and 4 wherein a ratio of the amount (B mmol) of dioctylamine to the amount (A mmol) of diglycolic anhydride is 1.0≦B/A≦1.2, the DODGAA's were obtained in high yields while their Nd/Pr separation factor indicative of the separation ability of a metal extractant and the phase separation were satisfactory.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: