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

HRID 1666475Notes

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

Participants

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

concentrationThe reaction was concentrated
dissolutionthe residue was dissolved in ethyl acetate
additionWater was added
concentrationThe organic layer was concentrated
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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