Sodium Chloride → 7-(3-Bromophenyl)-9-azabicyclo[3.3.1]nonan-3-one

HRID 2061612Notes

Reaction equation

HRID 2061612 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][CH:14]3[NH:16][CH:10]([CH:11](C(OC)=O)[C:12](=[O:21])[CH:13]3C(OC)=O)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Na+].[Cl-]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:15][CH:14]3[NH:16][CH:10]([CH2:11][C:12](=[O:21])[CH2:13]3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 70230991Dimethyl 7-(3-bromophenyl)-3-oxo-9-azabicyclo[3.3.1]nonane-2,4-dicarboxylate

Product 1

HCID 673036667-(3-Bromophenyl)-9-azabicyclo[3.3.1]nonan-3-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Dimethyl 7-(3-bromophenyl)-3-oxo-9-azabicyclo[3.3.1]nonane-2,4-dicarboxylate (89) and NaCl (61.22 g, 1.05 mol) in DMSO (200 ml) and water (10 ml) was placed into a preheated oil bath at 160° C. After stirring for 14 h, the solution was cooled to ambient temperature and exhaustively extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and concentrated to afford compound 90.

Workup

  1. extractionexhaustively extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b4e305ce1ec41c4b85240dccfa7e403
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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