Triphenylphosphine → (S)-N-[1-(4-{1-[4-(Tetrahydro-2H-pyran-4-yloxy)-phenyl]-piperidin-4-yl}-phenyl)-ethyl]-acetamide

HRID 1470750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470750
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:26]1[CH2:31][CH2:30][CH:29](O)[CH2:28][CH2:27]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[O:26]1[CH2:31][CH2:30][CH:29]([O:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][CH:11]([C:14]4[CH:15]=[CH:16][C:17]([C@@H:20]([NH:22][C:23](=[O:25])[CH3:24])[CH3:21])=[CH:18][CH:19]=4)[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH2:28][CH2:27]1

Komponenten

6

Edukt 4

HCID 11776Triphenylphosphine2×HCID 74956Tetrahydro-4H-pyran-4-olHCID 97268Di-tert-butyl azodicarboxylate2×HCID 67125424(S)-N-{1-(4-[1-(4-Hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide2×

Produkt 1

HCID 67970857(S)-N-[1-(4-{1-[4-(Tetrahydro-2H-pyran-4-yloxy)-phenyl]-piperidin-4-yl}-phenyl)-ethyl]-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

34 mg (0.10 mmol) (S)—N-{1-(4-[1-(4-Hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (compound 1.48), 15 mg (0.15 mmol) tetrahydro-4H-pyran-4-ol and 39 mg (0.15 mmol) triphenylphosphine on solid support are suspended in 2 mL anhydrous THF at 0° C. 35 mg (0.15 mmol) di-tert-Butyl azodicarboxylate are added and the mixture is allowed to warm to rt. Stirring is continued over night followed by addition of 0.5 equivalents of triphenylphosphine on solid support and 0.5 equivalents of di-tert-butyl azodicarboxylate. After stirring for 2 h at rt, the mixture is filtered over basic aluminum oxide and washed with DMF/MeOH (9:1). After evaporation the residue is purified using reversed phase HPLC (water/MeOH, 0.1% TFA) to yield the desired product.

Aufarbeitung

  1. waitis continued over night
  2. stirringAfter stirring for 2 h at rt
  3. filtrationthe mixture is filtered over basic aluminum oxide
  4. washwashed with DMF/MeOH (9:1)
  5. customAfter evaporation the residue
  6. customis purified

Quellen und Nachweise

ORD-Eintrag
ord-eafa32d498e84516b84491696f3aebe7
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006450B2

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