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

HRID 1761182

Reaction equation

HRID 1761182 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-methylenetetrahydropyridine-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-2e19c62e03b64d19a9ccd16cd604c688
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Linked notes

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