3,4-dihydro-2H-pyran → HCID 86598946, Verbindung

HRID 2220372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220372
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@H:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1>ClCCl.C(OCC)(=O)C.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@@H:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:26][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:7]=1

Komponenten

7

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 24824073HCID 24824073, Verbindung

Produkt 1

HCID 86598946HCID 86598946, VerbindungAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)KatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-phenylethyl]carbamate (3.20 g) in dichloromethane (40 ml) were added 3,4-dihydro-2H-pyran (1.28 g) and pyridinium p-toluenesulfonate (191 mg) at room temperature and the mixture was stirred at the same temperature for 5 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give tert-butyl [2-(4-bromophenyl)ethyl][(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]carbamate (4.11 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-187fdb01855c498597af2630825d58f8
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417060B2

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