Sodium hydride → N-Boc-O-(cyclohexylmethyl)-L-Serine

Participants

Reaction Conditions

Reaction Steps

Undercooling with ice, sodium hydride (60%, 3.95 g) was added to a solution of (2S)-3-hydroxy-2-t-butoxycarbonylaminopropanoic acid (10.11 g) in dimethylformamide (200 ml, hereinafter abbreviated as DMF). The mixture was stirred for 30 minutes at 0° C. Under cooling with ice, (bromomethyl)cyclohexane (9.0 ml) was added dropwise to the reaction mixture and tetrabutylammonium iodide (910 mg) was added thereto. The mixture was stirred for 23 hours at room temperature. Further, (bromomethyl)cyclohexane (2.1 ml) was added dropwise to the reaction mixture. The mixture was stirred for 4 hours. (Bromomethyl)cyclohexane (2.1 ml) was added dropwise to reaciton mixture again. The mixture was stirred for 25 hours at room temperature. The reaction mixture was concentrated and the residue was diluted with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and saturated aqueous sodium chloride, successively, dried over anhydrous magnesium sulfate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (chloroform:methanol=97:3) to give the title compound (2.52 g) having the following physical data.

Provenance & Evidence