Triethylamine → Tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylate

HRID 2172298Notes

Reaction equation

HRID 2172298 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH:13]=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(N(CC)CC)C>CO.[Pt](=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 71259576tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 86687410Tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylateYield 56.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate J, 8.45 g, 20.80 mmol) and platinum(IV) oxide (0.472 g, 2.080 mmol) in 40 mL MeOH was placed under 45 psi (4559.6 kpa) H2 for 2 hours. The reaction mixture was filtered through a plug of diatomaceous earth and was concentrated. The resulting residue was taken up in 10 mL THF, was treated with di-tert-butyl dicarbonate (10.40 ml, 10.40 mmol) followed by triethylamine (2.90 ml, 20.80 mmol) and was allowed to stir for 4 hours. Concentration and purification of the resulting residue by silica gel column chromatography (0 to 10% EtOAc/heptane) gave tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylate (4.812 g, 11.79 mmol) as a clear oil. [M+Na]+=432.0

Workup

  1. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth
  2. concentrationwas concentrated
  3. concentrationConcentration and purification of the resulting residue by silica gel column chromatography (0 to 10% EtOAc/heptane)

Sources & evidence

ORD record
ord-1b00d401810948b4a6a4dc2ccb56f1c4
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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