Tert-butyl[(1s,5r,6r)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate → (+/-)-[(1S,5R,6R)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetic acid

HRID 551612Notes

Reaction equation

HRID 551612 reaction equation
[NH2:1][CH2:2][C@@:3]1([CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])[CH2:9][C@H:8]2[C@@H:4]1[CH:5]=[CH:6][CH2:7]2>Cl.C(OCC)(=O)C>[NH2:1][CH2:2][C@@:3]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][C@H:8]2[C@@H:4]1[CH:5]=[CH:6][CH2:7]2

Participants

3

Reactant 1

HCID 66803936Tert-butyl[(1s,5r,6r)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

Product 1

HCID 49802949(+/-)-[(1S,5R,6R)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetic acidYield 35%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

A 4 N hydrochloric acid-ethyl acetate solution (10 mL) was added to tert-butyl(±)-[(1S,5R,6R)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (0.99 g, 4.17 mmol), and the mixture was stirred at room temperature for 1 hour. 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 and then dried under reduced pressure to obtain the compound of interest as a white powder (211.6 mg, 35%).

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
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e1d6ed678f6b4cf48a7d019d7f3a657b
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

Loading…