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Sulfuric Acid → Tert-butyl 9-benzyl-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

HRID 471281
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 471281
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([CH2:20][NH:21][CH2:22][C:23]([CH3:25])=[CH2:24])([OH:19])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:26](=[O:29])(O)[O-:27].[Na+]>C(#N)C>[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]2([O:19][C:23]([CH3:25])([CH3:24])[CH2:22][N:21]([C:26]([O:27][C:7]([CH3:12])([CH3:8])[CH3:6])=[O:29])[CH2:20]2)[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 579889841-Benzyl-4-((2-methylallylamino)methyl)piperidin-4-ol

Produkt 1

HCID 57989295Tert-butyl 9-benzyl-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Concentrated sulfuric acid (12 ml) was added to 1-benzyl-4-((2-methylallylamino)methyl)piperidin-4-ol (Example 271, step a) (2.2 g) and the mixture was allowed to stand for 2 hours at room temperature. The reaction mixture was treated with ice/water (100 mL) followed by solid sodium bicarbonate, portionwise, until the mixture was basic. Acetonitrile (50 mL) was added followed by BOC-anhydride (1.925 g) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was extracted with ethyl acetate (×2) and the combined organics were dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography, eluting with 1% methanol in dichloromethane switching to 1% methanol in dichloromethane with 1% triethylamine. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.8 g.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with ethyl acetate (×2)
  2. dry with materialthe combined organics were dried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude product was purified by flash silica chromatography
  6. washeluting with 1% methanol in dichloromethane switching to 1% methanol in dichloromethane with 1% triethylamine
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4707f4a4ebf244e28e5edc85da83f9b1
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08629271B2

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