tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylate

HRID 1473363Notes

Reaction equation

HRID 1473363 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>CCO.C(Cl)Cl.[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

5

Reactant 1

HCID 71259576tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 86687410Tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylateYield 39.7%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (from Step 1 of Intermediate VV; 2.435 g, 5.99 mmol) in 20 mL EtOH was treated with platinum(iv) oxide (0.136 g, 0.599 mmol) and was placed under 45 psi H2 for one hour. LC/MS showed mostly product and de-brominated product. The reaction mixture was diluted with DCM and was filtered through diatomaceous earth. The filtrate was concentrated then purified directly by column chromatography (0 to 15% EtOAc/heptane) yielding tert-butyl 4-(2-bromo-5-(trifluoromethyl)phenyl)piperidine-1-carboxylate (0.970 g, 2.376 mmol, 39.6% yield). m/z (ESI) 431.0 (M+Na)+.

Workup

  1. filtrationwas filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated
  3. customthen purified directly by column chromatography (0 to 15% EtOAc/heptane)

Sources & evidence

ORD record
ord-5e08a022aba647a29dc978b664edfb59
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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