HCID 131728906, compound → HCID 67200613, compound

HRID 551651Notes

Reaction equation

HRID 551651 reaction equation
[NH2:1][CH2:2][C@@:3]1([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH2:9][C@H:8]2[C@@H:4]1[CH:5]=[C:6]([CH:10]([CH2:12][CH3:13])[CH3:11])[CH2:7]2>Cl.C(OCC)(=O)C>[NH2:1][CH2:2][C@@:3]1([CH2:14][C:15]([OH:17])=[O:16])[CH2:9][C@H:8]2[C@@H:4]1[CH:5]=[C:6]([CH:10]([CH2:12][CH3:13])[CH3:11])[CH2:7]2

Participants

3

Reactant 1

HCID 131728906HCID 131728906, compound

Product 1

HCID 67200613HCID 67200613, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

Tert-butyl(±)-[(1S,5R,6R)-6-aminomethyl-3-sec-butylbicyclo[3.2.0]hept-3-en-6-yl]acetate (2.26 g, 7.7 mmol) was dissolved in a 4 N hydrochloric acid-ethyl acetate solution (30 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 (0.98 g, 54%).

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-70ed4e52e32d48fabf4c732e809f7d76
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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