Triphenylphosphine → HCID 18700148, Verbindung

HRID 2289355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289355
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[C:4]([O:17][C:18]([F:21])([F:20])[F:19])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH:51](O)[CH2:50][CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH:51]([O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:12])[CH3:11])=[C:4]([O:17][C:18]([F:21])([F:19])[F:20])[CH:3]=2)[CH2:50][CH2:49]1)=[O:47])([CH3:44])([CH3:42])[CH3:43]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 18700104HCID 18700104, Verbindung

Produkt 1

HCID 18700148HCID 18700148, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 4-hydroxy-1-(tert-butyldimethylsilyloxymethyl)-2-trifluoromethoxybenzene (3.2 g, 10 mmol) from Step 4 above and triphenylphosphine (3.9 g, 15 mmol) in THF (50 mL) at 0° C. was added a solution of N-tert-butyloxycarbonyl-4-piperidinol (3.0 g, 15 mmol) and DEAD (2.6 g, 15 mmol) in THF (25 mL) dropwise over a period of 1 h. The mixture was stirred at 0° C. for 3 h and then at ambient temperature for 12 h. The solvent was removed under reduced pressure and the residue was suspended in ether. The solid triphenylphosphine oxide was removed by filtration and the filtrate was purified by pressurized silica gel column chromatography using a gradient elution of 5-10% EtOAc:hexanes as eluant to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-1-(tert-butyldimethylsilyloxy-methyl)-2-trifluoromethoxybenzene as a colorless gum.

Aufarbeitung

  1. waitat ambient temperature for 12 h
  2. customThe solvent was removed under reduced pressure
  3. customThe solid triphenylphosphine oxide was removed by filtration
  4. customthe filtrate was purified by pressurized silica gel column chromatography
  5. washa gradient elution of 5-10% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-65564d230cf84dac90c3fce118a828d9
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090805

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