Aluminium lithium hydride → 4-[((S)-4,4-difluoro-pyrrolidin-2-ylmethyl)-amino]-adamantan-1-ol

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Reaction Steps

Lithium aluminium hydride (0.51 g) was added in portions to the solution of (S)-4,4-difluoro-pyrrolidine-2-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide (1.2 g) in THF (15 mL) at RT. The reaction mixture was refluxed for 24 h. The reaction mixture was quenched with saturated aqueous sodium sulfate solution (15 mL) at 0° C., filtered through Celite® and extracted with ethyl acetate (3×10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under high vacuum using rotary evaporator to give a crude material, which was purified through column chromatography (3% MeOH:DCM, silica 100-200 mesh, Diameter of column—2.5 cm, Height of silica—approx. 7 inch) to afford the desired 4-[((S)-4,4-difluoro-pyrrolidin-2-ylmethyl)-amino]-adamantan-1-ol as a white solid (0.5 g).

Provenance & Evidence