Triphenylphosphine → Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

HRID 2265880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2265880
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:20][C:21]1[CH:51]=[CH:50][C:24]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([N:35]3[CH2:44][CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[C:40]([OH:45])[CH:41]=4)[CH:36]3[C:46]([O:48][CH3:49])=[O:47])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1.[N:52]1([CH2:58][CH2:59]O)[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:25][C:26]2[CH:27]=[CH:28][C:29]([S:32]([N:35]3[CH2:44][CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[C:40]([O:45][CH2:59][CH2:58][N:52]5[CH2:57][CH2:56][O:55][CH2:54][CH2:53]5)[CH:41]=4)[CH:36]3[C:46]([O:48][CH3:49])=[O:47])(=[O:33])=[O:34])=[CH:30][CH:31]=2)=[CH:50][CH:51]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylateHCID 68679822Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylate

Produkt 1

HCID 68680877Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydroisoquinoline-1-carboxylateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

667 mg (2.0 mmol) of polymer-bound PPh3 (3 mmol/g) are introduced into 2 ml of THF and, at room temperature, 229 mg (0.5 mmol) of methyl 2-[4-(4-fluorophenoxy)-benzenesulfonyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (3B), 242 μl (2.0 mmol) of 2-morpholin-4-ylethanol and 311 μl (2.0 mmol) of DEAD are added. After one hour, the mixture is filtered and the filtrate is concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane→dichloromethane/methanol 98:2), resulting in 53% of the title compound.

Aufarbeitung

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is chromatographed on silica gel (dichloromethane→dichloromethane/methanol 98:2)

Quellen und Nachweise

ORD-Eintrag
ord-b30bb2b706ba449197875fb5540bdb4d
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858619B2

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