2-Methoxypropene → (4S,5R)-Tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1487449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487449
[F:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:4]([OH:12])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1.CO[C:23]([CH3:25])=[CH2:24]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl>[F:1][CH2:2][C@@H:3]1[C@@H:4]([C:5]2[CH:6]=[CH:7][C:8]([I:11])=[CH:9][CH:10]=2)[O:12][C:23]([CH3:25])([CH3:24])[N:13]1[C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20]

Komponenten

5

Edukt 2

HCID 83002-MethoxypropeneHCID 71050029Tert-butyl ((1R,2S)-3-fluoro-1-hydroxy-1-(4-iodophenyl)propan-2-YL)carbamate

Produkt 1

HCID 73424774(4S,5R)-Tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylateAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 1 L round bottom flask containing tert-butyl ((1R,2S)-3-fluoro-1-hydroxy-1-(4-iodophenyl)propan-2-yl)carbamate (24.4 g, 61.8 mmol) is charged with CH2Cl2 (250 mL) followed by 2-methoxypropene (9.0 mL, 92.8 mmol). The solution is cooled via ice bath and para toluene sulfonic acid (59 mg, 0.31 mmol) added. The reaction is stirred for 2 hours at room temperature then quenched with saturated sodiumbicarbonate solution (200 mL). The organics were separated, dried over MgSO4 and concentrated to give the title compound (26.5 g): 1H NMR (400 MHz, CDCl3) 7.73 (d, 2H), 7.20 (d, 2H), 5.08 (d, 1H), 5.03-4.69 (m, 1H), 4.54-4.31 (m, 1H), 3.91-3.68 (m, 1H), 1.70 (s, 3H), 1.58 (s, 3H), 1.50 (s, 9H).

Aufarbeitung

  1. temperatureThe solution is cooled via ice bath
  2. customthen quenched with saturated sodiumbicarbonate solution (200 mL)
  3. customThe organics were separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9290d6bc586a43d6927b6e6ae477d2f3
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428528B2

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