Toluene → HCID 68733649, Verbindung

HRID 387518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387518
C1(C)C=CC=CC=1.[CH2:8]([C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C.CO[CH:42]1[N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:45]([CH3:55])([CH3:54])[CH2:44][CH2:43]1>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:8]([C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:30])[C@@H:22]([C@H:42]1[N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:45]([CH3:55])([CH3:54])[CH2:44][CH2:43]1)[C:23]1[CH:24]=[CH:25][C:26]([Br:29])=[CH:27][CH:28]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 54374212HCID 54374212, VerbindungHCID 59564912HCID 59564912, Verbindung

Produkt 1

HCID 68733649HCID 68733649, VerbindungAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

TiCl4 in toluene (3.52 mL, 3.52 mmol) was added to a solution of (R)-4-benzyl-3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one (1.26 g, 3.35 mmol) in DCM (30 mL) at −78° C. DIEA (0.64 mL, 3.69 mmol) was then added to the cold stirring solution. The reaction was stirred at −78° C. for 15 minutes, followed by the addition of a solution of tert-butyl 5-methoxy-2,2-dimethylpyrrolidine-1-carboxylate (1.00 g, 4.36 mmol, see Example F) in DCM (10 mL). The reaction was then warmed to −10° C. and stirred for 2 hours. The reaction was quenched with a saturated NH4Cl solution (20 mL), and the organic fraction was isolated, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography to give (S)-tert-butyl 5-((R)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-bromophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (1.63 g, 85%) as a solid.

Aufarbeitung

  1. temperatureThe reaction was then warmed to −10° C.
  2. stirringstirred for 2 hours
  3. customThe reaction was quenched with a saturated NH4Cl solution (20 mL)
  4. customthe organic fraction was isolated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf3cf9d6a3d94336816484f8a32dce5a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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