Trifluoroacetic acid → HCID 15895218, compound

HRID 1384977Notes

Reaction equation

HRID 1384977 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH2:18][C@H:17]([CH2:21][O:22][C:23]2[C:28]([CH3:29])=[CH:27][C:26]([Br:30])=[CH:25][C:24]=2[CH3:31])[CH2:16]1)=O)(C)(C)C>ClCCl>[Br:30][C:26]1[CH:27]=[C:28]([CH3:29])[C:23]([O:22][CH2:21][C@H:17]2[CH2:18][CH2:19][CH2:20][NH:15][CH2:16]2)=[C:24]([CH3:31])[CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15895217HCID 15895217, compound

Product 1

HCID 15895218HCID 15895218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (80 mL) was added dropwise during 20 minutes to a solution of (S)-N-(tert-butoxycarbonyl)-3-(4-bromo-2,6-dimethylphenoxymethyl)piperidine (37.0 g, 92.9 mmol) in dichloromethane (250 mL) at a temperature of 5° C. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. The solvent was then evaporated and the residue partitioned between 25% aqueous sodium hydroxide (200 mL) and ether (500 mL). The organic layer was removed and the aqueous phase extracted with additional ether (2×300 mL). The combined ether layers were washed with brine (100 mL), stirred over magnesium sulfate for 2 hours, and filtered to give a solution of (S)-3-(4-bromo-2,6-dimethylphenoxymethyl)piperidine.

Workup

  1. additionAfter the addition
  2. customThe solvent was then evaporated
  3. customthe residue partitioned between 25% aqueous sodium hydroxide (200 mL) and ether (500 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous phase extracted with additional ether (2×300 mL)
  6. washThe combined ether layers were washed with brine (100 mL)
  7. stirringstirred over magnesium sulfate for 2 hours
  8. filtrationfiltered

Sources & evidence

ORD record
ord-5c312f9befa34e02b27d587e5f519f14
Source dataset
uspto-grants-2001_07
Patent number
US06262078B1

Reaction notes

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