{(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester → (3R,5R)-3-((R)-1-benzyloxyethyl)-5-(4-chlorophenyl)morpholine

Participants

Reaction Steps

A 4 N hydrochloric acid/ethyl acetate solution (40 mL) of {(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester (2.61 g) was stirred for 1 hour at room temperature. The solvent was removed under a vacuum, and methanol (30 mL) was added. Under ice-cooling, sodium cyanoborohydride (733 mg) was added, and the resultant was stirred overnight at room temperature. The solvent was removed under a vacuum, and the resultant was diluted with ethyl acetate and washed with saturated sodium bicarbonate aqueous solution and brine in sequence, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified with silica gel column chromatography (heptane/ethyl acetate 95/5→3/2), and the title compound (1.435 g) was obtained. The physical property values are as follows.

Provenance & Evidence