Lawesson's reagent → HCID 57473378, compound

HRID 871901Notes

Reaction equation

HRID 871901 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15](=O)[NH2:16])([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([C:15](=[S:27])[NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 53393793tert-Butyl 4-carbamoyl-4-methylpiperidine-1-carboxylate

Product 1

HCID 57473378HCID 57473378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-carbamoyl-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (2.1 g, 8.7 mmol) in THF (30 mL) was added Lawesson's reagent (3.5 g, 8.7 mmol) at room temperature. The mixture was heated at 50° C. for 3 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was washed with saturated NaHCO3, and brine. After drying (Na2SO4), the solvent was removed in vacuo, and the residue was purified by silica column chromatography with EtOAc/hexanes to afford the desired product.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed in vacuo
  3. customthe residue was partitioned between EtOAc and H2O
  4. washThe organic layer was washed with saturated NaHCO3, and brine
  5. dry with materialAfter drying (Na2SO4)
  6. customthe solvent was removed in vacuo
  7. customthe residue was purified by silica column chromatography with EtOAc/hexanes

Sources & evidence

ORD record
ord-ae0ba642a29740f99b43d13b9b78b6d2
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

Loading…