Ethyl Acetate → HCID 54374690, compound

HRID 465361Notes

Reaction equation

HRID 465361 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([OH:17])[CH2:14][CH2:13][C@H:12]1[C:18]([O:20]C)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:22](C1C=CC(COC(C2C(C)=NC(S)=NC=2C)=O)=CC=1)([O-:24])=[O:23].[C:44](OCC)(=O)C>CO.O1CCOCC1.[C].[Pd]>[OH:17][C@H:15]1[CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][C:5]([N+:22]([O-:24])=[O:23])=[CH:6][CH:7]=2)=[O:10])[C@H:12]([C:18]([CH3:44])=[O:20])[CH2:13][CH2:14]1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 140810631-Benzyl 2-methyl (2S,5R)-5-hydroxypiperidine-1,2-dicarboxylateHCID 178433548HCID 178433548, compound

Product 1

HCID 54374690HCID 54374690, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5.7 g (19.43 mmol) of (2S,5R)-1-benzyloxycarbonyl-5-hydroxy-2-methoxycarbonylpiperidine, which was prepared by the procedure described in P.D. Bailey et al., Tetrahedron Letters. 29, 2231 (1988), in 250 ml of methanol was added 570 mg of 5% palladium-carbon, and the mixture was hydrogenated at atmospheric pressure and room temperature for 1 hours. The catalyst was removed by filtration, and the solvent was removed. To a solution of this residue in 30 ml of dioxane was dropwise added a solution of 6.85 g (21.45 mmol) of p-nitrobenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine in 50 ml of dioxane, and the mixture was stirred for 1.5 hours at room temperature. To the reaction mixture was added 300 ml of ethyl acetate, the organic layer was washed successively with 50 ml of 1N HCl(×2), 50 ml of water and saturated aqueous sodium chloride. After the extract was dried over anhydrous sodium sulfate, the solvent was removed. The residue was purified by silica gel column chromatography (Wakogel® C-300, elution with ethyl acetate - hexane system) to give 5.81 g (yield: 88%) of the title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed
  3. washthe organic layer was washed successively with 50 ml of 1N HCl(×2), 50 ml of water and saturated aqueous sodium chloride
  4. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified by silica gel column chromatography (Wakogel® C-300, elution with ethyl acetate - hexane system)

Sources & evidence

ORD record
ord-13c0ac206fda49e294d3a754b2ebc70b
Source dataset
uspto-grants-1992_10
Patent number
US05153188

Reaction notes

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