HCID 131728927, compound → HCID 67200004, compound

HRID 551704Notes

Reaction equation

HRID 551704 reaction equation
[NH2:1][CH2:2][C@@:3]1([CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH2:9][C@@:8]2([CH3:10])[C@@H:4]1[CH:5]=[CH:6][CH2:7]2>Cl.C(OCC)(=O)C>[NH2:1][CH2:2][C@@:3]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:9][C@@:8]2([CH3:10])[C@H:4]1[CH:5]=[CH:6][CH2:7]2

Participants

3

Reactant 1

HCID 131728927HCID 131728927, compound

Product 1

HCID 67200004HCID 67200004, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

Tert-butyl(±)-[(1S,5S,6R)-6-(aminomethyl)-1-methylbicyclo[3.2.0]hept-3-en-6-yl]acetate (0.90 g, 3.6 mmol) was dissolved in a 4 N hydrochloric acid-ethyl acetate solution (20 mL), and the solution was stirred at room temperature for 2 hours. Then, the solvent was distilled off under reduced pressure. The residue was suspended by the addition of dichloromethane. To the suspension, triethylamine was then added dropwise, and the resulting powder was collected by filtration. The obtained powder was washed with dichloromethane to obtain the compound of interest as a white powder (0.33 g, 47%).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionThe residue was suspended by the addition of dichloromethane
  3. additionTo the suspension, triethylamine was then added dropwise
  4. filtrationthe resulting powder was collected by filtration
  5. washThe obtained powder was washed with dichloromethane

Sources & evidence

ORD record
ord-23b35316f175458f954e27537bc7c773
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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