HCID 131728909, compound → HCID 67199495, compound

HRID 551660Notes

Reaction equation

HRID 551660 reaction equation
[NH2:1][CH2:2][C@@:3]1([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:9][C@H:8]2[C@@H:4]1[CH:5]=[C:6]([CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:7]2>Cl.C(OCC)(=O)C>[NH2:1][CH2:2][C@@:3]1([CH2:15][C:16]([OH:18])=[O:17])[CH2:9][C@H:8]2[C@@H:4]1[CH:5]=[C:6]([CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:7]2

Participants

3

Reactant 1

HCID 131728909HCID 131728909, compound

Product 1

HCID 67199495HCID 67199495, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

Tert-butyl(±)-[(1S,5R,6R)-6-aminomethyl-3-cyclopentylbicyclo[3.2.0]hept-3-en-6-yl]acetate (2.00 g, 6.5 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 (0.70 g, 43%).

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-98c901eb77364492b7daf52147e9614b
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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