Triphenylphosphine → HCID 58992609, Verbindung

HRID 602182

Reaktionsgleichung

Reaktionsgleichung von HRID 602182
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][C:26]2[CH:25]=[CH:24][C:23]([C:20]3[CH:19]=[CH:18][C:17]([Cl:16])=[CH:22][CH:21]=3)=[CH:28][CH:27]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 915894'-Chloro-4-biphenylolHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 87147022ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene

Produkt 1

HCID 58992609HCID 58992609, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(tert-Butoxycarbonyl)piperidin-3-ylmethanol (323 mg, 1.50 mmol) and 4′-chloro-4-hydroxybiphenyl (307 mg, 1.50 mmol) were suspended in tetrahydrofuran (15 mL). To this suspension, triphenylphosphine (608 mg, 2.25 mmol) was added and the mixture was stirred at room temperature for 10 min. A 40% diethylazodicarboxylate/toluene solution (1.36 mL, 3.00 mmol) was then added and the mixture was stirred at room temperature for 16 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=50:1->10:1) gave 401 mg (67%) of the desired compound as a colorless powder.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed with brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=50:1->10:1)

Quellen und Nachweise

ORD-Eintrag
ord-d32fc68c954446ddb5732ec013f856ee
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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