4-(2-Acetoxyethyl)-1-tert-butoxycarbonylpiperidine → 4-(2-Acetoxyethyl)-1-tert-butoxycarbonylpiperidin-2-one

HRID 1739003Notes

Reaction equation

HRID 1739003 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=[O:3])[CH3:2].I([O-])(=O)(=O)=[O:21].[Na+]>C(OCC)(=O)C.O.[Ru](=O)(=O)(=O)=O>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:11](=[O:21])[CH2:12]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 218400164-(2-Acetoxyethyl)-1-tert-butoxycarbonylpiperidineHCID 23667635Sodium periodate2×

Product 1

HCID 218400254-(2-Acetoxyethyl)-1-tert-butoxycarbonylpiperidin-2-one

Reagents, catalysts & solvents 3

HCID 119079Ruthenium tetroxideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The product from Step B (0.275 g, 1.01 mmol) was dissolved in ethyl acetate (5 mL). A solution of sodium periodate in water (0.5 g in 5 mL) and ruthenium tetroxide (13 mg, 0.10 mmol) was added, and the heterogeneous reaction stirred vigorously overnight at room temperature. An additional portion of sodium periodate in water was added (0.5 g in 5 mL) and the reaction stirred overnight. The reaction was quenched with 10% sodium thiosulfate, and filtered through celite. The phases were separated, and the organic phase dried over magnesium sulfate. Filtration and evaporation gave the title compound.

Workup

  1. customthe heterogeneous reaction
  2. stirringthe reaction stirred overnight
  3. customThe reaction was quenched with 10% sodium thiosulfate
  4. filtrationfiltered through celite
  5. customThe phases were separated
  6. dry with materialthe organic phase dried over magnesium sulfate
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-e9f33ce16e3a4a5a9567fa8dacac5ba3
Source dataset
uspto-grants-1999_10
Patent number
US05965578

Reaction notes

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