Trimethylphosphine → HCID 117600153, compound

Participants

Reaction Steps

The crude (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2-amine (1.29 g, 3.63 mmol) was dissolved in THF (27 mL). A THF solution of trimethylphosphine (3.63 mL, 3.63 mmol) was added. After 5 h, the mixture was quenched with 35 mL of 1M aqueous HCl, and the mixture was stiffed overnight. The mixture was then neutralized with saturated NaHCO3 (70 mL) and the aqueous layer mixture was extracted with EtOAc (500 mL). The organic layer was washed with saturated brine (35 mL), dried over MgSO4 and concentrated to afford crude (S)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine, which was used without purification in the next step. MS m/z=330 [M+H]+.

Provenance & Evidence