Diglycolamine → HCID 123226547, compound

Participants

Reaction Conditions

Reaction Steps

2-(2-Aminoethoxyl)ethanol (0.7 g, 5 eq.) was added to a solution of 2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl 4-methylbenzenesulfonate (0.5 g, 1 eq.) in dry acetonitrile (10 mL) and the reaction mixture was heated to 75° C. for 3 h and then at 85° C. for 1 h. The acetonitrile was removed in vacuo. The crude residue was redissolved in DCM (25 mL) and washed with water (25 mL) the aqueous phase was re-extracted with DCM (2×25 mL). The combined organic phases were washed with water (50 mL), dried (MgSO4), filtered and concentrated at reduced pressure to a pale yellow oil (0.4 g). The crude product was purified by silica column chromatography eluting with 10% methanolic ammonia in DCM to give 0.19 g (50%) of 18 as a colourless oil. 13C NMR (CDCl3) δ 156.1, 72.5, 70.2, 70.1, 61.9, 49.2, 49.0, 40.5, 28.4. ESMS (C13H28N2O5) [M+H]+ calc. 293.2076. found 293.2076.

Provenance & Evidence