Hexane → (3S)-3-carbobenzoxyamino-5-methyl-1-hexene

Participants

Reaction Steps

To a solution of 12 g of methyltriphenylphosphonium bromide in 100 ml of dry tetrahydrofuran was added 19.5 ml of n-butyl lithium (as a 1.6 mole hexane solution) under an argon atmosphere, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was cooled below 5° C., and a solution of 7.5 g of N-carbobenzoxy-L-leucinal in 20 ml of dry tetrahydrofuran was added to the reaction mixture. The mixture was stirred for 1 hour at room temperature. An aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: dichloromethane) to obtain 1.6 g of (3S)-3-carbobenzoxyamino-5-methyl-1-hexene as a colorless oil.

Provenance & Evidence