Sodium Sulfite → 1,1-Dimethylethyl 4-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate

HRID 1785273

Reaktionsgleichung

Reaktionsgleichung von HRID 1785273
C=C1CC[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C[N+]1([O-])CC[O:19]CC1.S([O-])([O-])=O.[Na+].[Na+].[O:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.O>C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[OH:19][C:32]1([CH2:33][OH:29])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:30][CH2:31]1

Komponenten

7

Edukt 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 27568081-Boc-4-MethylenepiperidineHCID 21881883Oxolane--water (1/1)

Produkt 1

HCID 225945581,1-Dimethylethyl 4-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 98 mg of t-butyl 4-methylenetetrahydro-pyridine-1(2H)-carboxylate in 2 ml of tetrahydrofuran-water (1:1), 88 mg of N-methyl morpholine-oxide and 0.1 ml of 2% osmium tetraoxide were added at 0° C., followed by 2 hours' stirring at the same temperature. Adding sodium sulfite to the reaction liquid, the reaction liquid was further stirred for 30 minutes, diluted with ethyl acetate, washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 115 mg of the title compound was obtained.

Aufarbeitung

  1. customthe reaction liquid
  2. stirringwas further stirred for 30 minutes
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationDistilling the solvent off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dfed5481dc9c401e99dea675414aa0e6
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504432B2

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