Lithium naphthalenide → (1R*,2R*,5R*)-8-Benzyl-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

Participants

Reaction Steps

Lithium naphthalenide (200 ml, 0.6M in teterahydrofuran) was added dropwise into a −78° C. solution of (1R*,2R*,5S*,6R*)-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 4; 25 g, 57.7 mmol) in THF (350 ml). The mixture was quenched by addition of saturated ammonium chloride and warmed to room temperature The reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic layer was washed (×2) with water then dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5, 15 and 40% ethyl acetate/iso-hexanes to yield the title compound (14.3 g, 84.6%).

Provenance & Evidence