HCID 66803709, compound → HCID 25222055, compound

HRID 551614Notes

Reaction equation

HRID 551614 reaction equation
C([O:5][C:6](=[O:17])[CH2:7][C@@:8]1([CH2:15][NH2:16])[CH2:14][C@@H:13]2[C@H:9]1[CH:10]=[CH:11][CH2:12]2)(C)(C)C>Cl.C(OCC)(=O)C>[NH2:16][CH2:15][C@:8]1([CH2:7][C:6]([OH:17])=[O:5])[CH2:14][C@@H:13]2[C@H:9]1[CH:10]=[CH:11][CH2:12]2

Participants

3

Reactant 1

HCID 66803709HCID 66803709, compound

Product 1

HCID 25222055HCID 25222055, compoundYield 551%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A 4 N hydrochloric acid-ethyl acetate solution (200 mL) was added to tert-butyl[(1R,5S,6S)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (17.53 g, 7.4 mmol), and the mixture was stirred at room temperature for 1.5 hours. Then, the solvent was distilled off under reduced pressure. The residue was suspended in dichloromethane. To the suspension, triethylamine was added dropwise, and the resulting powder was collected by filtration, then washed with dichloromethane, and then dried to obtain a white powder A (6.85 g). From the filtrate, the solvent was distilled off under reduced pressure. To the residue, a 4 N hydrochloric acid-ethyl acetate solution (200 mL) was then added again, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the residue was suspended in dichloromethane. To the residue, triethylamine was added dropwise, and the resulting powder was collected by filtration, then washed with dichloromethane, and then dried to obtain a white powder B (2.48 g). This white powder B was combined with the above-obtained white powder A and washed with ethanol and ethyl acetate to obtain the compound of interest as a white powder (7.39 g, 55%).

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. additionTo the suspension, triethylamine was added dropwise
  3. filtrationthe resulting powder was collected by filtration
  4. washwashed with dichloromethane
  5. customdried
  6. customto obtain a white powder A (6.85 g)
  7. distillationFrom the filtrate, the solvent was distilled off under reduced pressure
  8. additionTo the residue, a 4 N hydrochloric acid-ethyl acetate solution (200 mL) was then added again
  9. stirringthe mixture was stirred at room temperature for 2 hours
  10. distillationThe solvent was distilled off under reduced pressure
  11. additionTo the residue, triethylamine was added dropwise
  12. filtrationthe resulting powder was collected by filtration
  13. washwashed with dichloromethane
  14. customdried
  15. customto obtain a white powder B (2.48 g)
  16. washwashed with ethanol and ethyl acetate

Sources & evidence

ORD record
ord-156c4e8e7dd746858bc4815c082748d7
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

Loading…