Biphenyl → 5-Thiazol-2-yl-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 1038032

Reaktionsgleichung

Reaktionsgleichung von HRID 1038032
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.CC(C)([O-])C.[Na+].[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]2[CH2:26][C@H:21]1[CH2:22][NH:23]2)=[O:19])([CH3:16])([CH3:15])[CH3:14].C1(C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH:24]2[CH2:26][CH:21]1[CH2:22][N:23]2[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Komponenten

9

Edukt 4

HCID 7095BiphenylHCID 764302-BromothiazoleHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 669396205-Thiazol-2-yl-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl esterAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromothiazole (200 mg, 1.22 mmol), palladium acetate (15 mg, 0.06 mmol), sodium tert-butoxide (217 mg, 2.26 mmol), (S,S) 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (280 mg, 1.4 mmol) and 2-Di-t-butylphosphino)-biphenyl (37 mg, 0.118 mmol) was stirred in dioxane (10 ml) at 80° C. for overnight. The reaction was cooled, diluted with ethyl acetate (40 ml) and H2O (50 ml). The organic layer was separated, dried (Na2SO4), filtered and solvent evaporated. The residue was purified by chromatography eluting with 5% MeOH/DCM yielding product as a white solid. (180 mg, 52% yield)

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with 5% MeOH/DCM yielding product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-5f0d31b3dc66434a9d00699ec56389b2
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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