Triphenylphosphine → (5S)-5-(Aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

Beteiligte Stoffe

Reaktionsschritte

A mixture of (5R)-5-(azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (2.22 g, INTERMEDIATE 9) and triphenylphosphine (3.44 g) was heated to 65° C. for 6 h in 444 ml of tetrahydrofuran and 56 ml of water. The sample was then cooled to room temperature, and concentrated in vacuo. The residue was purified via column chromatography on a Biotage Horizon 40M column eluting with 100% ethyl acetate (5 column volumes) to remove excess triphenylphosphine and triphenylphosphine oxide, followed by 100% methanol (5 column volumes), to provide the title compound (1.74 g, 87%). Mass spectrum (ESI) 228.1 (M+1).

Herkunft & Nachweise