Sodium Hydroxide → HCID 117856476, compound

HRID 1497292Notes

Reaction equation

HRID 1497292 reaction equation
[F:1][CH:2]([F:16])[C@H:3]1[CH2:8][C@H:7]([OH:9])[C@H:6]([NH:10]C(=O)C)[C@@H:5]([OH:14])[C@@H:4]1[OH:15].[OH-].[Na+]>CCO.O>[NH2:10][C@H:6]1[C@@H:7]([OH:9])[CH2:8][C@H:3]([CH:2]([F:1])[F:16])[C@@H:4]([OH:15])[C@@H:5]1[OH:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117856797HCID 117856797, compound

Product 1

HCID 117856476HCID 117856476, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-((1S,2R,3R,4S,6S)-4-(difluoromethyl)-2,3,6-trihydroxycyclohexyl)acetamide (176 mg, 1.48 mmol) in EtOH (2 mL) and water (3 mL) was added NaOH (736 mg, 18.4 mmol). The mixture was heated at reflux for 2 h. Solvents were evaporated and the residue was purified by silica gel column chromatography, eluted with 20% 2 M NH3 MeOH solution in DCM to give the product (1R,2R,3S,4S,6S)-3-amino-6-(difluoromethyl)cyclohexane-1,2,4-triol (90.0 mg, 62%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customSolvents were evaporated
  4. customthe residue was purified by silica gel column chromatography
  5. washeluted with 20% 2 M NH3 MeOH solution in DCM

Sources & evidence

ORD record
ord-02d569135618445b9a489a8e77ee69bb
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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