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Triethyl phosphonoacetate → 3-Ethoxycarbonylmethylene-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester

HRID 1455552
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1455552
[CH2:1]([O:3][C:4](=[O:14])[CH2:5]P(OCC)(OCC)=O)[CH3:2].[H-].[Na+].[C:17]([O:21][C:22]([N:24]1[CH:29]2[CH2:30][CH2:31][CH2:32][CH:25]1[CH2:26][C:27](=O)[CH2:28]2)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH:25]2[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:28][C:27](=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:26]2)=[O:23])([CH3:20])([CH3:18])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 45790088N-Boc-9-azabicyclo[3.3.1]nonan-3-one

Produkt 1

HCID 684432003-Ethoxycarbonylmethylene-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

0.54 ml of (diethoxy-phosphoryl)-acetic acid ethyl ester are added dropwise to a suspension of 108 mg of NaH (55% in mineral oil) in 5 ml of THF at 0°. The mixture obtained is stirred and 650 mg of 3-oxo-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester in 5 ml of THF are slowly added. The mixture obtained is stirred at 60° C. for 3 days, diluted with c-HEX and washed with 1M aqueous NaH2PO4 and saturated aqueous NaHCO3 solution. The organic layer obtained is dried, solvent is evaporated and the evaporation residue obtained is subjected to chromatography on silica gel. 3-Ethoxycarbonylmethylene-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester is obtained in the form of an oil. 13C-NMR: 171.79, 154.45, 154.27, 133.38, 132.77, 127.11, 126.30, 79.64, 79.54, 61.03, 61.00, 48.59, 47.20, 46.81, 45.22, 42.72, 33.61, 33.42, 32.59, 32.17, 30.73, 30.07, 28.87, 28.57, 28.13, 16.48, 14.59.

Aufarbeitung

  1. customThe mixture obtained
  2. customThe mixture obtained
  3. stirringis stirred at 60° C. for 3 days
  4. additiondiluted with c-HEX and
  5. washwashed with 1M aqueous NaH2PO4 and saturated aqueous NaHCO3 solution
  6. customThe organic layer obtained
  7. customis dried
  8. customsolvent is evaporated
  9. customthe evaporation residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-3f776ac227b247348c05611328957d6b
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07482462B2

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