Water → HCID 86724268, compound

HRID 873726Notes

Reaction equation

HRID 873726 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-ff844a5757474913bb9d4cc778155bd3
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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