Sodium Carbonate → HCID 71208290, Verbindung

HRID 872199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872199
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C@@H:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25]([N:28]1[CH2:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH2:30][CH2:29]1)(=[O:27])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C@@H:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:31]4[CH2:32][CH2:33][N:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:29][CH:30]=4)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 86675682(R)-4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 71208290HCID 71208290, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of (R)-4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.40 g), 1-methanesulfonyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine (0.38 g), 2 M aqueous Na2CO3 solution (1.3 mL), and 1,4-dioxane (8 mL) is sparged with argon for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.10 g) is added and the mixture is stirred in a microwave oven at 170° C. for 1 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:7→0:1) to give the title compound. Mass spectrum (ESI+): m/z=464 [M+H]+.

Aufarbeitung

  1. customis sparged with argon for 5 min
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.10 g) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater is added
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. extractionThe combined extract
  7. washis washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:7→0:1)

Quellen und Nachweise

ORD-Eintrag
ord-2b827c81146b4ca78315c767cd81cc84
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975277B2

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