HCID 131729682, compound → tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate

HRID 1028073Notes

Reaction equation

HRID 1028073 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[O-:10])[CH:5]=[N:6][CH:7]=1>C(O)(=O)C.[Rh].[Pt](=O)=O>[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([NH:8][C:9](=[O:10])[O:11][C:2]([CH3:3])([CH3:7])[CH3:1])[CH2:3]1

Participants

5

Reactant 1

HCID 131729682HCID 131729682, compound

Product 1

HCID 57433105tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methylpyridin-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-methylpiperidin-3-ylcarbamate. LCMS (m/z): 215.1 (MH+).

Workup

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

Sources & evidence

ORD record
ord-b22fd6cd72794c018da72c44f08b0cdb
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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