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Triphenylphosphine → HCID 21963144, Verbindung

HRID 2211822
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2211822
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:3]1=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]1.N(C([O-])=O)=NC([O-])=O>O1CCCC1>[C:53]([O:52][C:50]([N:47]1[CH2:48][CH2:49][N:44]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[O:1][CH:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=3)[C:3]2=[O:17])[CH2:45][CH2:46]1)=[O:51])([CH3:56])([CH3:54])[CH3:55]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylateHCID 21963156HCID 21963156, VerbindungHCID 51573101N-carboxylatoiminocarbamate

Produkt 1

HCID 21963144HCID 21963144, VerbindungAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 241 mg (0.983 mmol) 3-hydroxy-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one, 15 mL dry tetrahydrofuran, 645 mg (2.45 mmol) triphenylphosphine, and 328 mg (1.18 mmol) N-(2-hydroxyphenyl)-4-t-butoxycarbonyl-piperazine. A solution of 398 mg (1.97 mmol) disopropyl azodicarboxylate in 10 mL dry tetrahydrofuran was added dropwise over 5 minutes, and the reaction stirred at room temperature overnight. The reaction was quenched with aqueous sodium bicarbonate solution, separated, and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was chromatographed on silica using hexane/ethyl acetate as eluant to afford 320 mg (64%) of an oil.

Aufarbeitung

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. customThe reaction was quenched with aqueous sodium bicarbonate solution
  3. customseparated
  4. extractionthe aqueous layer extracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica

Quellen und Nachweise

ORD-Eintrag
ord-a1f52a8665fa4ff2a436ff2e2f708639
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07101885B2

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