Fluorotrimethylsilane → trimethylsilyl (2S,4R)-N-(chloroacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate

HRID 220745

Reaktionsgleichung

Reaktionsgleichung von HRID 220745
C[Si](C)(C)[N:3]1[CH2:7][C@H:6]([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][C@H:4]1[C:13]([O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Cl:22][CH2:23][C:24](F)=[O:25].[Si](F)(C)(C)C>ClCCl>[Cl:22][CH2:23][C:24]([N:3]1[CH2:7][C@H:6]([O:8][Si:9]([CH3:10])([CH3:11])[CH3:12])[CH2:5][C@H:4]1[C:13]([O:15][Si:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:25]

Komponenten

5

Edukt 3

HCID 9869FluorotrimethylsilaneHCID 53254852-chloroacetyl FluorideHCID 21632773(4R)-1-(Trimethylsilyl)-4-(trimethylsilyloxy)-L-proline trimethylsilyl ester

Produkt 1

HCID 46841616trimethylsilyl (2S,4R)-N-(chloroacetyl)-4-(trimethylsilyloxy)pyrrolidine-2-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Into a solution of trimethylsilyl (2S,4R)—N-trimethylsilyl-4-(trimethylsilyloxy)-pyrrolidine-2-carboxylate (5.22 g, 15.0 mmol) in 15 ml of anhydrous dichloromethane was drop wise added a solution of chloroacetyl fluoride in 5 ml of dichloromethane with vigorous stirring at room temperature. Exothermic reaction occurred with liberation of Me3SiF. The reaction mixture was stirred at room temperature for 2 h and then the reaction mixture was evaporated to dryness at reduced pressure, which gave 5.02 g (yield 95%) of trimethylsilyl (2S,4R)—N-chloroacetyl-4-(trimethylsilyloxy)pyrrolidine-2-carboxylate as off-white solid: 1H-NMR (CDCl3) δ 0.02 (m, 9H), 0.19 (m, 9H), 1.80-2.4 (m, 2H), 3.3-3.8 (m, 2H), 3.8-4.0 (m, 2H), 4.2-4.6 (m, 2H): 13C-NMR (CDCl3) δ −0.32 (CSi), −0.05 (CSi), 37.91, 41.81, 55.30, 59.21, 70.31, 165.13, 171.78.

Aufarbeitung

  1. customExothermic reaction
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. customthe reaction mixture was evaporated to dryness at reduced pressure, which

Quellen und Nachweise

ORD-Eintrag
ord-f85a8b93b0454446ae06a9caccd060f0
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08203003B2

Verknüpfte Notizen

Wird geladen…