Triethylamine → (S)-2,2-Dimethyl-4-[4-(4-phenoxy-phenoxy)-benzyl]-oxazolidine 3-carboxylic acid tert-butyl ester

HRID 1669502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669502
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:23]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][C:33]3[CH:34]=[CH:35][C:30]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:31][CH:32]=3)=[CH:18][CH:19]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27343774-Phenoxyphenylboronic acidHCID 10425336tert-Butyl (S)-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Produkt 1

HCID 67349978(S)-2,2-Dimethyl-4-[4-(4-phenoxy-phenoxy)-benzyl]-oxazolidine 3-carboxylic acid tert-butyl esterAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-4-(4-Hydroxy-benzyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.250 g, 0.846 mmol), 4-Phenoxyphenyl-boronic acid (0.181 g, 0.846 mmol), and triethylamine (0.59 mL, 4.232 mmol) in anhydrous dichloromethane (DCM) (20.8 mL) at room temperature under an atmosphere of nitrogen was added copper (II) acetate (0.154 g, 0.846 mmol), and the resulting mixture was stirred at room temperature for about 60 hours. The reaction mixture was washed with 20 mL of water and 20 mL of DCM and filtered. The DCM layer was then extracted. The aqueous layer was re-extracted with DCM (2×15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent was removed in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain the product (0.030 g, 8%).

Aufarbeitung

  1. washThe reaction mixture was washed with 20 mL of water and 20 mL of DCM
  2. filtrationfiltered
  3. extractionThe DCM layer was then extracted
  4. extractionThe aqueous layer was re-extracted with DCM (2×15 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto obtain the crude mixture, which
  9. customwas purified by of silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-46d820b0e7fc49c884e0c95a34efbfc7
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989480B2

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