Water → 1-[(1R,5S,6R)-6-(4-aminophenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-propan-1-one

HRID 1173060Notes

Reaction equation

HRID 1173060 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:16][C@@H:15]3[C@H:11]2[CH2:12][N:13]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:14]3)=[CH:6][CH:5]=1)([O-])=O.O>CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:16][C@@H:15]3[C@H:11]2[CH2:12][N:13]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:14]3)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 962WaterHCID 673648491-((1R,5S,6R)-6-(4-nitro-phenyl)-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one

Product 1

HCID 673664421-[(1R,5S,6R)-6-(4-aminophenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-propan-1-oneYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.21 g of 1-((1R,5S,6R)-6-(4-nitro-phenyl)-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one (4.44 mmol) were dissolved in 50 ml of methanol, 8.0 g of stannous dichloride SnCl2×H2O (35.46 mmol) were added, and the reaction was stirred under refluxing conditions for 2 h. The solvent was evaporated and the residue portioned between 1 N aqueous sodium hydroxide and ethyl acetate. This mixture was filtered, the two phases were separated, and the aqueous layer was extracted with ethyl acetate and dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to yield 0.94 g of the product as a mixture of 72% para and 28% ortho substituted product which was used in the next step without further separation.

Workup

  1. customThe solvent was evaporated
  2. filtrationThis mixture was filtered
  3. customthe two phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate and dichloromethane
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c826cedcb12a491fb2f2d98c806dac16
Source dataset
uspto-grants-2010_11
Patent number
US07834048B2

Reaction notes

Loading…