Triphenylphosphine → HCID 9953505, Verbindung

HRID 985722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985722
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]([S:36]([CH3:39])(=[O:38])=[O:37])[C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:23][CH:22]=1.[N:40]1([CH2:46][CH2:47][CH2:48]O)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>O1CCCC1>[N:40]1([CH2:46][CH2:47][CH2:48][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:28]([S:36]([CH3:39])(=[O:38])=[O:37])[C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:23][CH:22]=2)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 22507783HCID 22507783, Verbindung

Produkt 1

HCID 9953505HCID 9953505, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of immobilized triphenylphosphine resin (330 mg, 1.0 meq (Fluka)), and the product of Step E (140 mg, 0.50 mmol) in tetrahydrofuran (6.0 mL) was treated with 3-(piperdin-1-yl)propanol (143 mg, 1.0 mmol) followed by diethylazidodicarboxylate (0.16 mL, 1.1 mmol). The reaction was shaken for 20 hr. and filtered. The filtrate was concentrated in vacuo and the residue purified by silica gel chromatography (methanol/ethyl acetate) to afford pure title compound (97 mg). MS (ESI) m/z 413 (MH+); 1H-NMR (CDCl3) δ 8.13 (d, 1H), 7.59 (d, 1H), 7.50 (d, 2H), 7.36 (m, 2H), 6.97 (d, 2H), 6.68 (s, 1H), 4.08 (t, 2H), 2.72 (s, 3H), 2.4 (m, 6H), 1.63 (m, 6H), 1.45 (m, 2H).

Aufarbeitung

  1. filtrationand filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by silica gel chromatography (methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a5270f2385eb43ec857a213fafe2697b
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872834B2

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