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

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.

1. temperatureThe reaction mixture was cooled below 5° C.
2. stirringThe mixture was stirred for 1 hour at room temperature
3. extractionthe mixture was extracted with ethyl acetate
4. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
5. dry with materialdried over anhydrous magnesium sulfate
6. customevaporated under reduced pressure
7. customThe residue was purified by silica gel flash column chromatography (eluent: dichloromethane)

ORD record

ord-29ca6d9c606244eabe0da15ae0bdc89d

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04841067