Potassium Hydroxide → (S)-(9-amino-2-bromo-7-iodo-9H-xanthen-9-yl)methanol

In a 350-mL resealable vessel, the (S)-2′-bromo-7′-iodospiro[oxazolidine-4,9′-xanthen]-2-one (11 g, 24.02 mmol) was dissolved in 1:1 MeOH-dioxane (160 mL). Aqueous KOH (5 M, 48.0 mL, 240 mmol) was added. The vessel was sealed and placed in a 105° C. oil bath. After 24 h, the reaction was concentrated to remove the MeOH and most of the dioxane. The residue was diluted with water (200 mL) and the aqueous phase was extracted with 5% MeOH-DCM (4×200 mL). The organics were combined, washed with dilute brine (35 mL), dried over sodium sulfate and concentrated. The residue was purified by chromatography (1.5% MeOH/DCM) to afford (S)-(9-amino-2-bromo-7-iodo-9H-xanthen-9-yl)methanol (3.84 g, 8.89 mmol).

1. customThe vessel was sealed
2. customplaced in a 105° C.
3. concentrationthe reaction was concentrated
4. customto remove the MeOH
5. additionThe residue was diluted with water (200 mL)
6. extractionthe aqueous phase was extracted with 5% MeOH-DCM (4×200 mL)
7. washwashed with dilute brine (35 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customThe residue was purified by chromatography (1.5% MeOH/DCM)

ORD record

ord-afd4f1f069454a5f90b8cd2920ca173d

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08497264B2