Water → HCID 86724268, compound

HRID 594872Notes

Reaction equation

HRID 594872 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C:6]1([CH2:8][CH2:7]1)[C:5]2([NH:19]S(C(C)(C)C)=O)[C:14]([F:18])([F:17])[CH2:15][OH:16].Cl.O1CCOCC1.C([O-])(O)=O.[Na+].O>C1COCC1.CCO.[Cl-].[Na+].O>[NH2:19][C:5]1([C:14]([F:18])([F:17])[CH2:15][OH:16])[C:6]2([CH2:8][CH2:7]2)[CH2:9][O:10][C:11]2[C:4]1=[CH:3][C:2]([Br:1])=[CH:13][CH:12]=2

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86724269HCID 86724269, compound

Product 1

HCID 86724268HCID 86724268, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 21873804Tetrahydrofuran ethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Under ice cooling, to a solution of N-[6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-4H-spiro[chromene-3,1′-cyclopropan]-4-yl]-2-methylpropane-2-sulfinamide (4.60 g, 10.5 mmol) in THF-EtOH (50% v/v, 46 mL) was added 4M HCl/dioxane (13.1 mL, 52.5 mmol), and the mixture was stirred for 3 hours at room temperature. Under ice cooling, saturated aqueous NaHCO3, H2O and brine were added to the mixture, and then the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (EtOAc/hexane=50:50-100:0) to give 2-(4-amino-6-bromo-4H-spiro[chromene-3,1′-cyclopropan]-4-yl)-2,2-difluoroethanol (2.28 g).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (EtOAc/hexane=50:50-100:0)

Sources & evidence

ORD record
ord-84734a63e87544e183216ed93eb57b60
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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