Methyl morpholine oxide → Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

HRID 2300159Notes

Reaction equation

HRID 2300159 reaction equation
[CH2:1]([C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:22]CC1.O1CCCC1.[OH2:31]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[OH:31][CH:2]([CH2:3][OH:22])[CH2:1][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22744545Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

9.83 g of tert-butyl 4-allyl-4-hydroxy-1-piperidinecarboxylate was dissolved in 60 ml tetrahydrofuran/water (9:1), a solution (2.5 wt %, 2 ml) of osmium tetraoxide in tert-butyl alcohol and 6.68 g of N-methylmorpholine-N-oxide were added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was evaporated, and the resulting residue was partitioned into ethyl acetate and water, washed with brine and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give 9.11 g of tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was partitioned into ethyl acetate and water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-4eb4ea90dcb64690ae507c2e0db255d6
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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