tert-butyl N-(5-(trifluoromethyl)pyridin-3-yl)carbamate → tert-butyl N-[(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamate

HRID 1920181Notes

Reaction equation

HRID 1920181 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>C(O)(=O)C.[Rh].[Pt](=O)=O>[F:18][C:2]([F:1])([F:17])[C@H:3]1[CH2:8][NH:7][CH2:6][C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:4]1

Participants

5

Reactant 1

HCID 59455734tert-butyl N-(5-(trifluoromethyl)pyridin-3-yl)carbamate

Product 1

HCID 73977851tert-butyl N-[(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamate

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl 5-(trifluoromethyl)pyridin-3-ylcarbamate (3 g, 14 mmol) in glacial acetic acid (50 mL) was added 5% Rhodium on active carbon (0.5 g) and Platinum(IV) oxide (0.5 g) in the hydrogenation steel bomb. The mixture was sealed and hydrogenated at 200 psi and 70° C. for 48 h. the mixture was filtered through Celite and concentrated to give cis-(+/−)-tert-butyl 5-(trifluoromethyl)piperidin-3-ylcarbamate. LCMS (m/z): 269.1 (MH+).

Workup

  1. customThe mixture was sealed
  2. filtrationthe mixture was filtered through Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a6b3c5cf030c4ac4985e0b431a337e29
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

Loading…