Trifluoroacetic acid → 4-{[5-Cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}piperidine

HRID 1689806Notes

Reaction equation

HRID 1689806 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[C:17]([C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[N:18][O:19][C:20]=2[CH:21]2[CH2:23][CH2:22]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:21]1([C:20]2[O:19][N:18]=[C:17]([C:24]3[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=3[Cl:30])[C:16]=2[CH2:15][O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59369325Tert-butyl 4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)piperidine-1-carboxylate

Product 1

HCID 593693344-{[5-Cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}piperidineYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a cooled (ice bath) 500 mL flask under nitrogen, is added a solution of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester (16 g, 34.3 mmol) in dichloromethane (80 mL). This is followed by dropwise addition of trifluoroacetic acid (80 mL) (added over 30 minutes). The reaction is stirred at room temperature for 90 min. The solvent is removed under vacuum, EtOAc is added (400 mL), and the mixture is washed with 2 N NaOH (2×250 mL) and brine. The organic layer is dried over MgSO4, filtered and evaporated to obtain the title compound as a brown oil (11.78 g, 93%). MS (m/e): 367 (M+1)

Workup

  1. temperatureIn a cooled (ice bath) 500 mL flask under nitrogen
  2. customThe solvent is removed under vacuum, EtOAc
  3. additionis added (400 mL)
  4. washthe mixture is washed with 2 N NaOH (2×250 mL) and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-edc98b54f2294e9db1b7dbd91d83cb6d
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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