tert-butyl N-(5-(trifluoromethyl)pyridin-3-yl)carbamate → HCID 59455772, compound

HRID 716192Notes

Reaction equation

HRID 716192 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[N:7][CH:8]=1.[H][H]>[Pt](=O)=O.[Rh].C(O)(=O)C>[F:18][C:2]([F:1])([F:17])[CH:3]1[CH2:8][NH:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:4]1

Participants

6

Reactant 2

HCID 59455734tert-butyl N-(5-(trifluoromethyl)pyridin-3-yl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59455772HCID 59455772, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

In a 50 mL hastalloy metal reactor, tert-butyl (5-(trifluoromethyl)pyridin-3-yl)carbamate (600 mg, 2.29 mmol) was treated with glacial acetic acid (10 mL), platinum (IV) oxide (250 mg, 1.10 mmol) and rhodium (5 wt. % (dry) on carbon, degussa type, 250 mg, 2.43 mmol) and hydrogenated at 200 psi hydrogen at 70° C. for 23 h. The reaction mixture was cooled to RT and filtered through a 0.45 um acrodisc, washed with MeOH and concentrated under reduced pressure. The residue was treated with EtOAc and 2N NaOH and extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine and dried over MgSO4, filtered and concentrated to afford rac-tert-butyl (5-(trifluoromethyl)piperidin-3-yl)carbamate (490 mg, 1.83 mmol, 80%). MS (ESI, pos. ion) m/z: 269.1 (M+1). The crude material was used in the subsequent step without further purification.

Workup

  1. filtrationfiltered through a 0.45 um acrodisc,
  2. washwashed with MeOH
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was treated with EtOAc and 2N NaOH
  5. extractionextracted with EtOAc (3×25 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0af429e639354876aecb01fca7ed6cb4
Source dataset
uspto-grants-2015_11
Patent number
US09187486B2

Reaction notes

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