Hydrochloric Acid → [6-(Aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetic acid

HRID 2190983Notes

Reaction equation

HRID 2190983 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH2:10][CH:9]2[CH:5]1[CH:6]=[CH:7][CH2:8]2>C(OCC)(=O)C>[NH2:2][CH2:3][C:4]1([CH2:11][C:12]([OH:14])=[O:13])[CH2:10][CH:9]2[CH:5]1[CH:6]=[CH:7][CH2:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66803930Tert-butyl[6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

Product 1

HCID 66696942[6-(Aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetic acidYield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4 N solution of hydrochloric acid in ethyl acetate (10 mL) was added to tert-butyl [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-f4d87e29d90e4bec89ef39bb2f6ed065
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

Loading…