Water → HCID 15117211, compound

HRID 1029609Notes

Reaction equation

HRID 1029609 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([OH:16])([C:10]#[C:11][Si](C)(C)C)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O.C(=O)([O-])[OH:19].[Na+]>O1CCCC1.CN(C)C=O.S(=O)(=O)(O)O>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:10](=[O:19])[CH3:11])([OH:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15117210HCID 15117210, compound

Product 1

HCID 15117211HCID 15117211, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-acetyl-4-hydroxy-4-(2-trimethylsilylethynyl)piperidine (13 g) in a mixture of tetrahydrofuran (100 ml), water (25 ml) and N,N-dimethylformamide (10 drops) were added mercuric sulfate (1.6 g) and sulfuric acid (10 drops), and the resultant mixture was stirred at ambient temperature for 15 hours. After adjusting pH to around 8 with sodium hydrogen carbonate, the reaction mixture was filtered with "florisil" (trademark, made by Floridin Co.) and the residue was washed with ethyl acetate and tetrahydrofuran. Filtrate and washings were combined and evaporated in vacuo, and the residue was dissolved in ethyl acetate, dried over magnesium sulfate. Evaporation of the solvent gave 1,4-diacetyl-4-hydroxypiperidine (8.75 g).

Workup

  1. filtrationthe reaction mixture was filtered with "florisil" (trademark, made by Floridin Co.)
  2. washthe residue was washed with ethyl acetate and tetrahydrofuran
  3. customevaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-fa3117dbc20e430881113c2dc895964e
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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