Potassium tert-butoxide → (S)-2'-bromo-7'-iodospiro[morpholine-3,9'-xanthen]-5-one

HRID 931620Notes

Reaction equation

HRID 931620 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]([NH:19][C:20](=[O:23])[CH2:21]Cl)([CH2:17][OH:18])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+]>C(O)(CC)(C)C>[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([CH2:17][O:18][CH2:21][C:20](=[O:23])[NH:19]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 67382923(S)-N-(2-bromo-9-(hydroxymethyl)-7-iodo-9H-xanthen-9-yl)-2-chloroacetamide

Product 1

HCID 67439034(S)-2'-bromo-7'-iodospiro[morpholine-3,9'-xanthen]-5-oneYield 45.8%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

In a 500-mL flask (S)—N-(2-bromo-9-(hydroxymethyl)-7-iodo-9H-xanthen-9-yl)-2-chloroacetamide (4.52 g, 8.89 mmol) was dissolved in t-amyl alcohol (125 mL). Potassium t-butoxide (2.244 g, 20.00 mmol) was added. After 14 h, the reaction was concentrated. The residue was taken up in dilute aqueous NH4Cl (50 mL) and the aqueous phase was extracted with 5% MeOH-DCM (3×133 mL). The organics were combined, washed with dilute brine (25 mL), dried over sodium sulfate and concentrated. The material was purified through silica gel (500 mL) using 30% EtOAc-hexane to afford (S)-2′-bromo-7′-iodospiro[morpholine-3,9′-xanthen]-5-one (1.92 g, 4.07 mmol).

Workup

  1. concentrationthe reaction was concentrated
  2. extractionthe aqueous phase was extracted with 5% MeOH-DCM (3×133 mL)
  3. washwashed with dilute brine (25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe material was purified through silica gel (500 mL)

Sources & evidence

ORD record
ord-fe103aa7e5bc45b68dab4e69e89e8aa8
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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