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

HRID 1785273

Reaction equation

HRID 1785273 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dfed5481dc9c401e99dea675414aa0e6
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Linked notes

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