Phenol → 4-((2s)-2-Hydroxy-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propoxy)-phenol

HRID 1634790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634790
C([Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[CH:21][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.NCC1CCN([C:38]2[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:39]=2[S:46]([NH2:49])(=[O:48])=[O:47])CC1.[C:50]1(O)[CH:55]=[CH:54][CH:53]=[CH:52]C=1.CCC[CH2:60][N+:61](CCCC)(CCCC)CCCC.[F-]>CO.C1COCC1>[OH:28][C@@H:27]([CH2:29][NH:61][CH2:60][CH:54]1[CH2:53][CH2:52][N:49]([S:46]([C:39]2[CH:38]=[CH:43][C:42]([O:44][CH3:45])=[CH:41][CH:40]=2)(=[O:47])=[O:48])[CH2:50][CH2:55]1)[CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([OH:18])=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 996PhenolHCID 2724141Tetrabutylammonium FluorideHCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 18678703HCID 18678703, Verbindung

Produkt 1

HCID 102258704-((2s)-2-Hydroxy-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propoxy)-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane (0.078 g, 0.19 mmol) and an excess of and (4-aminomethyl-1-piperidinyl)-4-methoxybenzene-sulfonamide (0.109 g, 0.38 mmol) was heated as a solution in methanol at 60° C. for 24 hours. The reaction mixture was preabsorbed on silica gel and purified by flash chromatography (CH2Cl2—CH3OH, 19:1) to give the intermediate silyl-protected product. Deprotection to the phenol was accomplished by treatment of the silyl intermediate with 1M TBAF in THF. After stirring 15 minutes the solvent was evaporated and the product isolated by flash chromatography (CH2Cl2—CH3OH, 12:1) to give 0.049 g of the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was preabsorbed on silica gel
  2. custompurified by flash chromatography (CH2Cl2—CH3OH, 19:1)
  3. customto give the intermediate silyl-
  4. customwas evaporated
  5. customthe product isolated by flash chromatography (CH2Cl2—CH3OH, 12:1)

Quellen und Nachweise

ORD-Eintrag
ord-b916ab1570e34d02b5f3d20c2f717364
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506901B2

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