Potassium Carbonate → Tert-butyl 7-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 1374112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1374112
Cl.[CH:2]12[O:10][CH:6]([CH2:7][NH:8][CH2:9]1)[CH2:5][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]2.C([O-])([O-])=O.[K+].[K+].Cl[CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>CC#N>[CH3:28][C:27]([CH3:30])([CH3:29])[C:26](=[O:31])[CH2:25][N:8]1[CH2:7][CH:6]2[O:10][CH:2]([CH2:3][N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]2)[CH2:9]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 18540411Tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate hydrochloride

Produkt 1

HCID 18540396Tert-butyl 7-(3,3-dimethyl-2-oxobutyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate hydrochloride (Preparation A; 0.26 g, 1.0 mmol) and K2CO3 (1.45 g, 10.5 mmol) in MeCN (8 mL) was treated with 1-chloropinacolone (0.216 g, 1.6 mmol), and the mixture stirred at 40° C. overnight. The following morning, the temperature was raised to 50° C. for 4 h before the solids were filtered off from the mixture and the filtrate concentrated in vacuo. The crude product was dissolved in DCM and the solution was added to an ion-exchange solid phase extraction plug (10 g CBA (carboxylic acid on silica support)). After 1 h, the plug was washed with DCM (15 mL), after which the product was finally eluted with dichloromethane:MeOH:TEA (90:5:5). The solvents were evaporated to give 0.276 g (85.5%) of the sub-title compound.

Aufarbeitung

  1. customPreparation A
  2. temperatureThe following morning, the temperature was raised to 50° C. for 4 h before the solids
  3. filtrationwere filtered off from the mixture
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe crude product was dissolved in DCM
  6. additionthe solution was added to an ion-exchange solid phase extraction plug (10 g CBA (carboxylic acid on silica support))
  7. waitAfter 1 h
  8. washthe plug was washed with DCM (15 mL)
  9. washafter which the product was finally eluted with dichloromethane:MeOH:TEA (90:5:5)
  10. customThe solvents were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d74d4f1c4eee44ee8ea3aef6e469d730
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07164017B2

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