Boron tribromide → HCID 117600691, compound

Participants

Reaction Conditions

Reaction Steps

The crude (S)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthene]-2,7′-diamine (1.196 g, 3.63 mmol) was dissolved in dcm (100 mL) and the solution was cooled to 0° C. A DCM solution of boron tribromide (14.53 mL, 14.53 mmol) was added, and the reaction was warmed to RT. After 1.5 h, the reaction was quenched with 120 mL of 10:1 saturated NH4Cl and commercial NH4OH. The mixture was extracted with 5% MeOH-DCM (3×250 mL). The organics were combined, washed with dilute brine (50 mL), dried over MgSO4 and concentrated, affording 0.97 g of crude (S)-2,7′-diamino-4′-fluoro-5,6-dihydrospiro[[1,3]oxazine-4,9′-xanthen]-2′-ol, which was used without purification in the next step. MS m/z=316 [M+H]+.

Provenance & Evidence