Triphenylphosphine → 2-[4-(3,4-Dichloro-benzyl)-morpholin-2-ylmethyl]-isoindole-1,3-dione

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A mixture of 2-[(3,4-dichlorobenzyl)amino]ethanol (2.038 g) and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione (2.032 g) in tetrahydrofuran (3.3 ml) was stirred and heated at reflux under nitrogen. After 21.5 h more tetrahydrofuran (12.5 ml) was added and the mixture was cooled to 3° C. Triphenyl phosphine (2.793 g) was added and the mixture was stirred until all the solid had dissolved. Diisopropylazodicarboxylate (2.1 ml) was then added over 12 min maintaining the temperature at <7° C. After 2.25 h the mixture was allowed to warm to 22° C. After 5.3 h more triphenylphosphine (121 mg) and diisopropylazodicarboxylate (0.09 ml) were added. After 22.5 h the reaction mixture was concentrated to near dryness. Propan-2-ol (12 ml) was added and the concentration repeated, this was repeated once more. More propan-2-ol (12 ml) was added and the mixture was heated to 70° C. After 0.5 h the slurry was cooled to 22° C. and then after a further 2 h the product was collected by filtration. The bed was washed with propan-2-ol (2×4 ml) and then dried in vacuo at 40° C. to give the product, (2.622 g).

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