Sodium Hydroxide → HCID 117839410, compound

HRID 1477654Notes

Reaction equation

HRID 1477654 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH:12]([CH:11]2[C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117839224HCID 117839224, compound

Product 1

HCID 117839410HCID 117839410, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (40 mL) of 3-benzyl-6-(4-fluorophenyl)-3-azabicyclo[3.1.0]hexan-2-one (956 mg, 3.40 mmol) synthesized in Reference Synthesis Example 238, lithium aluminum hydride (258 mg, 6.80 mmol) was added at 0° C. and the resultant mixture was stirred under reflux by heating for 30 minutes. After completion of the reaction, 1 M sodium hydroxide aqueous solution was added to the reaction solution at 0° C. and extraction from the resultant mixture with dichloromethane was performed. The organic layer was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate=15/1→10/1) to obtain the title compound (593 mg, yield 66%).

Workup

  1. additionwas added at 0° C.
  2. temperatureunder reflux
  3. temperatureby heating for 30 minutes
  4. additionwas added to the reaction solution at 0° C.
  5. extractionextraction from the resultant mixture with dichloromethane
  6. customThe organic layer was purified by silica gel (amino-based) column chromatography (hexane/ethyl acetate=15/1→10/1)

Sources & evidence

ORD record
ord-9fe56e14ecd04db48d2ede7ff2fd47f7
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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