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

HRID 931618Notes

Reaction equation

HRID 931618 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C@:5]3([CH2:20][O:19]C(=O)[NH:17]3)[C:4]=2[CH:3]=1.[OH-].[K+]>CO.O1CCOCC1>[NH2:17][C@@:5]1([CH2:20][OH:19])[C:4]2[CH:3]=[C:2]([Br:1])[CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][C:8]([I:16])=[CH:9][CH:10]=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67383335(S)-2'-bromo-7'-iodospiro[oxazolidine-4,9'-xanthen]-2-one

Product 1

HCID 67383446(S)-(9-amino-2-bromo-7-iodo-9H-xanthen-9-yl)methanolYield 37%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-0ca07ccd5d0c4a80bf5ad0fa4ce9aa55
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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