(S)-(+)-N-(Boc)-2-methylpiperidine → HCID 12176154, Verbindung

HRID 1747103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747103
[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I([O-])(=O)(=O)=[O:16].[Na+]>C(OCC)(=O)C.O.O.[Ru](=O)=O>[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

6

Edukt 2

HCID 11019870(S)-(+)-N-(Boc)-2-methylpiperidineHCID 23667635Sodium periodate

Produkt 1

HCID 12176154HCID 12176154, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 16211523Ruthenium dioxide hydrateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ruthenium(IV) oxide hydrate (0.8 g, 0.006 mol) then a solution of N-BOC-6(S)-methyl-piperidine (4.00 g, 0.020 mol) in ethyl acetate (240 ml) were added to a solution of sodium periodate (21.36 g, 0.100 mole) in water (200 ml) and strongly stirred for 24 hours at room temperature under argon atmosphere. After separation the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried with magnesium sulfate and then treated with activated carbon, giving a colorless solution that was evaporated on a rotavapor at 30° C. The residue (3.98 g) was purified by silicagel (125 g) column chromatography with cyclohexane-ethyl acetate (1-1, v/v), furnishing a product (2.50 g, 59% yield) which according to its 1H-NMR spectrum was pure enough for the next reaction step.

Aufarbeitung

  1. customAfter separation the aqueous phase
  2. extractionwas extracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic phases were dried with magnesium sulfate
  4. additiontreated with activated carbon
  5. customgiving a colorless solution that
  6. customwas evaporated on a rotavapor at 30° C
  7. customThe residue (3.98 g) was purified by silicagel (125 g) column chromatography with cyclohexane-ethyl acetate (1-1

Quellen und Nachweise

ORD-Eintrag
ord-a0190b0be5604c1583bdb6e417bf05b1
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150558B2

Notizen zur Reaktion

Wird geladen…