Aluminium lithium hydride → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(8-(3-(azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane (1.11 g, 2.71 mmol) in THF (15 mL) at −78° C. under an atmosphere of nitrogen, a solution of lithium aluminium hydride (2.0M in THF, 2.8 mL, 5.60 mmol) was added drop wise. After stirring the reaction at −78° C. for 1 hour, the reaction mixture was warmed up to 0° C. for 1 hour. The reaction mixture was quenched with water (304 mL), 2M sodium hydroxide (304 mL) and water (304 mL×3). Anhydrous magnesium sulphate and ethyl acetate were added, and the reaction mixture filtered and concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 100% iso-hexane to 100% DCM to 25:1 DCM:methanol (0.63 g, 39% based on (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanol).

Provenance & Evidence