Ethanol → tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate

HRID 2368059Notes

Reaction equation

HRID 2368059 reaction equation
[CH3:1][C@H:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.C(O)C>C(O)(=O)C.[Pt]=O>[CH3:1][C@H:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 702EthanolHCID 57517478tert-Butyl [(1S)-1-methyl-2-(pyridin-4-yloxy)ethyl]carbamate

Product 1

HCID 57517479tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamateYield 76.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl [(1S)-1-methyl-2-(pyridin-4-yloxy)ethyl]carbamate (1.03 g) in acetic acid (10 mL)/ethanol (10 mL) was added platinum oxide (500 mg), and the reaction mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated. The obtained residue was dissolved in 0.5 M hydrochloric acid, and the solution was washed with ethyl acetate, basified with potassium carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give the title compound (805 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe obtained residue was dissolved in 0.5 M hydrochloric acid
  4. washthe solution was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c348968e42ff4034a9b3259e6b2fa7c6
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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