1,1-Dimethylethyl N-[(1R)-1-ethyl-3-oxopropyl]carbamate → HCID 15881262, compound

Participants

Reaction Steps

To a solution of ((R)-1-ethyl-3-oxo-propyl)carbamic acid tert-butyl ester (2.9 mmol; 584 mg) in THF (20 mL) is added a 1.44 M THF solution (11.6 mmol; 8.1 mL) of vinylmagnesium chloride under nitrogen at −78° C. After stirring for 30 minutes, the reaction mixture is warmed to room temperature and stirred for an additional 1.5 hours. Another 1.44 M THF solution (2.9 mmol; 2 mL) of vinylmagnesium chloride is added to the reaction mixture at room temperature. After stirring for additional 15 minutes, the solution is quenched by saturated aqueous ammonium chloride solution and extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give ((1R,3S)-1-ethyl-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester (130 mg, 20%); ESI-MS m/z: 174 [M+−tBu+2], Retention time 4.13 min (condition B).

Provenance & Evidence