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Sodium Hydroxide → Tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylate

HRID 1666475
Notes
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Reaction equation

HRID 1666475 reaction equation
Br[C:2]1([CH:15]([Br:33])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=3)[CH:17]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[OH-].[Na+]>CO>[Br:33][C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][N:24]=2)[CH:17]=1)=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66876019Tert-butyl 4-bromo-4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methyl)piperidine-1-carboxylate

Product 1

HCID 66876318Tert-butyl 4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylene)piperidine-1-carboxylateYield 55.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 4-bromo-4-(bromo(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methyl)piperidine-1-carboxylate (890 mg, 1.50 mmol) in MeOH (5 mL) was added 2N NaOH (3 mL). The reaction was stirred at 40° C. for 14 h. The reaction was concentrated and the residue was dissolved in ethyl acetate. Water was added and the pH was adjusted to 2 using concentrated HCl. The organic layer was concentrated and the residue was purified by silica gel column chromatography (0-5% MeOH/CH2Cl2) to afford the title compound (425 mg, 55% yield) as a white solid.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. additionWater was added
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by silica gel column chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-690996efae8845569e18668346e451cd
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044052B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes