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Sodium hydride → 3-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid N-(4-nitro-3-trifluoromethyl-phenyl)-hydrazide

HRID 1591703
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1591703
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]23[O:21][CH:20]2[CH:19]2[CH2:22][CH2:23][CH:16]3[CH2:17][CH2:18]2)=[O:14])=[CH:8][C:7]=1[C:24]([F:27])([F:26])[F:25])([O-:5])=[O:4].C1(P([NH:42]O)(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:13]([C:15]23[O:21][CH:20]2[CH:19]2[CH2:18][CH2:17][CH:16]3[CH2:23][CH2:22]2)=[O:14])[NH2:42])=[CH:8][C:7]=1[C:24]([F:27])([F:25])[F:26])([O-:5])=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 419256DiphenylphosphinylhydroxylamineHCID 235461863-Oxa-tricyclo[3.2.2.02,4] nonane-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide

Produkt 1

HCID 235461873-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid N-(4-nitro-3-trifluoromethyl-phenyl)-hydrazideAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

NaH (60% in mineral oil, 7.9 mg, 0.20 mmol, 1.4 eq) was added to the solution of 11E (50 mg, 0.14 mmol, 1 eq) in DMF (3 mL). The reaction mixture was heated at 70° C. for 2 h. The reaction was cooled to rt and diphenylphosphinylhydroxylamine (52 mg, 0.22 mmol, 1.6 eq, made according to the procedure of Colvin, E. W. et.al. Tetrahedron Lett. 23, 3835-6 (1982)) was added. The reaction mixture was stirred at rt overnight and quenched by addition of water (3 mL) and extracted with EtOAc (2×20 mL). The combined organics were washed with H2O (25 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 10% EtOAc/CH2Cl2 gave 8.0 mg (0.022 mmol, 15.4%) of compound 11F as a yellow solid. HPLC conditions: 93% at 3.54 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm).

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. addition23, 3835-6 (1982)) was added
  3. customquenched by addition of water (3 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with H2O (25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography on silica gel eluting with 10% EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-83f1c18afb0c479996ad48ddb5a43549
Quelldatensatz
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07291637B2

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