HCID 21896272, compound → HCID 86723674, compound

HRID 1775505Notes

Reaction equation

HRID 1775505 reaction equation
[Ce+4].[NH4+].[CH3:3][O:4][C@@H:5]1[C@@H:10]2[CH2:11][C@@H:7]([C:8](=[O:21])[N:9]2CC2C=CC(OC)=CC=2)[CH2:6]1>O.CC#N>[CH3:3][O:4][C@@H:5]1[C@@H:10]2[CH2:11][C@@H:7]([C:8](=[O:21])[NH:9]2)[CH2:6]1

Participants

5

Reactant 2

HCID 21896272HCID 21896272, compoundHCID 71112708HCID 71112708, compound

Product 1

HCID 86723674HCID 86723674, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ammonium cerium(IV) (3.3 g, 6.06 mmol) in water (10 mL) was added to (1S,4R,6S)-6-methoxy-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (527 mg, 2.02 mmol) in CH3CN (40 mL). The reaction mixture was stirred at ambient temperature for 2 h and extracted by EtOAc (60 mL). The organic extract was washed with water and brine, dried over Na2SO4, and evaporated to give the crude (1S,4R,6S)-6-methoxy-2-azabicyclo[2.2.1]heptan-3-one. MS (ESI+): m/z 142 (M+H+).

Workup

  1. extractionextracted by EtOAc (60 mL)
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-a320da5ee46b48a6b20c90d87580221e
Source dataset
uspto-grants-2016_02
Patent number
US09260452B2

Reaction notes

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