HCID 10909973, compound → HCID 55277934, compound

HRID 1954077Notes

Reaction equation

HRID 1954077 reaction equation
[N:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[C@@H:3]([C:8]([O:10]CC)=[O:9])[CH2:2]2>Cl>[N:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[C@@H:3]([C:8]([OH:10])=[O:9])[CH2:2]2

Participants

3

Reactant 1

HCID 10909973HCID 10909973, compound

Product 1

HCID 55277934HCID 55277934, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl (3R,4S)-1-azabicyclo[2.2.1]heptane-3-carboxylate (2.0 g, I. F. Cottrell, D. Hands, D. J. Kennedy, K. J. Paul, S. H. B. Wright and K. Hoogsteen, J. Chem. Soc. Perkin Trans. 1, 1991, 1091-1097) was dissolved in concentrated hydrochloric acid and heated under reflux for 5 hours. After cooling the solution was evaporated under reduced pressure and the residue re-evaporated from toluene (×3). Drying over phosphorous pentoxide and trituration with cold ethyl acetate/methanol gave the hydrochloride salt of (3R,4S)-1-azabicyclo[2.2.1]heptane-3-carboxylic acid (1.2g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling the solution
  4. customwas evaporated under reduced pressure
  5. customthe residue re-evaporated from toluene (×3)
  6. dry with materialDrying over phosphorous pentoxide and trituration with cold ethyl acetate/methanol

Sources & evidence

ORD record
ord-f36ee2bbfd944ec29f3d69fec5614353
Source dataset
uspto-grants-2000_09
Patent number
US06121281

Reaction notes

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