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

HRID 2300159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300159
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4eb4ea90dcb64690ae507c2e0db255d6
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498159B1

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