Dimethylformamide → HCID 117697690, Verbindung

HRID 1778478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778478
CC([O-])(C)C.[K+].[C:7](=O)([O:10]C)[O:8][CH3:9].[C:13]([O:17][C:18]([N:20]1[CH:25]2[CH2:26][C:27](=[O:29])[CH2:28][CH:21]1[CH2:22][O:23][CH2:24]2)=[O:19])([CH3:16])([CH3:15])[CH3:14].CN(C=O)C>C1(C)C=CC=CC=1>[CH3:9][O:8][C:7]([CH:26]1[C:27](=[O:29])[CH2:28][CH:21]2[N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])[CH:25]1[CH2:24][O:23][CH2:22]2)=[O:10]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 12021Dimethyl CarbonateHCID 185070529-Boc-7-oxa-9-azabicyclo[3.3.1]nonan-3-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 117697690HCID 117697690, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of t-BuOK (1.82 g, 16.26 mmol) in toluene (30 mL) was added dimethyl carbonate (0.98 g, 10.84 mmol). The mixture was heated at 90° C. for 5 mins, and then 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (1.3 g, 5.4 mmol) was added. After the resulting mixture was stirred at 90° C. for 30 mins, the mixture was turned to brown gel, and then DMF (1.5 mL) was added to get a brown solution. The mixture was stirred at 90° C. for 3 hours. After it was cooled to room temperature, silica gel (25 g, 100200 mesh) was added and the solvent was concentrated in vacuo. The residue was purified by flash column chromatography (EtOAc in PE 0%˜70%) to give 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-6,9-dicarboxylic acid 9-tert-butyl ester 6-methyl ester (Compound AO) as light yellow oil (0.8 g, 49%). LC/MS: calc'd 300 (MH+), exp 300 (MH+); 1HNMR (400 MHz, CDCl3) δ 1.40-1.45 (m, 9H), 2.29-2.41 (m, 1H), 2.68-2.84 (m, 1H), 3.47-3.79 (m, 7H), 3.88-3.96 (m, 0.5H), 4.09-4.16 (m, 0.3H), 4.30-4.45 (m, 1H), 4.55-4.67 (m, 0.8H), 11.86 (s, 0.3H).

Aufarbeitung

  1. customto get a brown solution
  2. stirringThe mixture was stirred at 90° C. for 3 hours
  3. temperatureAfter it was cooled to room temperature
  4. additionsilica gel (25 g, 100200 mesh) was added
  5. concentrationthe solvent was concentrated in vacuo
  6. customThe residue was purified by flash column chromatography (EtOAc in PE 0%˜70%)

Quellen und Nachweise

ORD-Eintrag
ord-f0bc95a41ac749d2aa176bdb86f1dc12
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266904B2

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