Potassium Carbonate → 3-[4-(Pyridin-2-yl-oxy)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester

HRID 40699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40699
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:11][CH:10]=2)O1.[C:23]([O:27][C:28]([N:30]1[CH:35]2[CH2:36][CH2:37][CH:31]1[CH:32]=[C:33](OS(C(F)(F)F)(=O)=O)[CH2:34]2)=[O:29])([CH3:26])([CH3:25])[CH3:24].[Cl-].[Li+].C([O-])([O-])=O.[K+].[K+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[C:23]([O:27][C:28]([N:30]1[CH:35]2[CH2:36][CH2:37][CH:31]1[CH:32]=[C:33]([C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:20][CH:21]=1)[CH2:34]2)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 226480948-Boc-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene2×HCID 672487012-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]pyridine

Produkt 1

HCID 674124983-[4-(Pyridin-2-yl-oxy)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl esterAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)phenoxy]pyridine (0.62 g, 2.1 mmol), 3-trifluoromethanesulfonyloxy-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester (0.75 g, 2.1 mmol) (intermediate 1), tetrakis(triphenylphosphine)-palladium (0.24 g, 0.21 mmol) and lithium chloride (0.107 g, 2.52 mmol) are placed in 10 ml of DME and 2.6 ml of a 2N aqueous solution of K2CO3. The reaction medium is refluxed for 16 h. After hydrolysis and extraction with ethyl acetate, the organic phase is dried over MgSO4 and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in heptane ranging from 0% to 30%. 0.45 g of expected 3-[4-(pyridin-2-yl-oxy)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acid tert-butyl ester is obtained.

Aufarbeitung

  1. temperatureThe reaction medium is refluxed for 16 h
  2. dry with materialthe organic phase is dried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe crude product obtained
  5. customis chromatographed on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-918059c66a0a4340975e82897c69135e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530477B2

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