Diethyl Ether → HCID 86586642, Verbindung

HRID 2088095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088095
[H-].[Na+].[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:17][C@@:11]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:12]([OH:27])[CH:13]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:34][C:35]([F:49])([F:48])[C:36]1[CH:37]=[C:38]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[CH2:39]Br.C(OCC)C>C1COCC1>[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([S:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)(=[O:19])=[O:20])[CH2:17][C@@:11]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:12]([O:27][CH2:39][C:38]1[CH:41]=[C:42]([C:44]([F:46])([F:47])[F:45])[CH:43]=[C:36]([C:35]([F:34])([F:48])[F:49])[CH:37]=1)[CH:13]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 69890684HCID 69890684, Verbindung

Produkt 1

HCID 86586642HCID 86586642, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (94 mg, 60% in oil, 2.45 mmol) was added to a stirred solution of (1R*,2S*,5S*,6R*)-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-en-2-ol (Description 5b; 256 mg, 0.6 mmol) and 3,5-bis(trifluoromethyl)benzyl bromide (0.8 ml) in dry THF (3 ml) at room temperature. The reaction mixture was stirred at +50° C. for 30 minutes, then cooled to room temperature and treated with diethyl ether (70 ml). The mixture was washed twice with water, brine. The combined organic extracts were dried (Na2SO4) and concentrated. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-30%) to give the title compound (400 mg, quant.).

Aufarbeitung

  1. washThe mixture was washed twice with water, brine
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-30%)

Quellen und Nachweise

ORD-Eintrag
ord-387098fcbee14ac99281774c36ca94fd
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727249B2

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