Trifluoroacetic acid → HCID 68533409, compound

HRID 401810Notes

Reaction equation

HRID 401810 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]2=[O:16])(C)(C)C.[C:18]([OH:24])([C:20]([F:23])([F:22])[F:21])=[O:19]>C(Cl)Cl>[F:21][C:20]([F:23])([F:22])[C:18]([OH:24])=[O:19].[NH2:7][CH:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]2=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68535128HCID 68535128, compound

Product 1

HCID 68533409HCID 68533409, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Oxo-bicyclo[2.2.2]oct-2-yl)-carbamic acid tert-butyl ester (Preparation 75, 279 g, 1.17 mol, 1.0 eq) was taken up in DCM (450 mL). TFA (416 mL, 5.60 mol, 4.8 eq) was added dropwise. On addition, the reaction warms to reflux while much gas evolves. The reaction mixture was kept at reflux temperature for 1 hour after which it was allowed to cool to room temperature overnight. The mixture was concentrated and the residue was taken up in DCM (50 mL) and then tert-butyl methyl ether (1.3 L) was added which resulted in a brown suspension. The solids were collected by filtration (P3) and were washed with tert-butyl methyl ether. The latter was dried in vacuo (40° C.) to furnish title compound as an off-white solid (272 g, 1.07 mol, 92%).

Workup

  1. additionOn addition
  2. temperatureto reflux while much gas evolves
  3. temperatureat reflux temperature for 1 hour after which it
  4. concentrationThe mixture was concentrated
  5. additiontert-butyl methyl ether (1.3 L) was added which
  6. customresulted in a brown suspension
  7. filtrationThe solids were collected by filtration (P3)
  8. washwere washed with tert-butyl methyl ether
  9. customThe latter was dried in vacuo (40° C.)

Sources & evidence

ORD record
ord-e45bafd565604a84b9b5ed03ef2f7976
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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