Hydrochloric Acid → (2S)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine

HRID 1090539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090539
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([OH:22])[CH2:19][C@H:18]1[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:16])[CH:12]=[CH2:13].Cl>ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O.C(N(CC)CC)C>[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C:20](=[O:22])[CH2:19][C@H:18]1[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])=[O:16])[CH:12]=[CH2:13]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 18639173(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine

Produkt 1

HCID 18639169(2S)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidineAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittel3×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

To a solution of oxalyl chloride (0.18 ml) in dichloromethane (10 ml) was added dropwise a solution of dimethyl sulfoxide (0.3 ml) in dichloromethane (2 ml) at -60° C. After stirring at -70° C. for 30 minutes, to the mixture was added dropwise a solution of (2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine (0.6 g) in dichloromethane (5 ml) at -60° C. After stirring at -70° C. for 30 minutes, to the mixture was added dropwise triethylamine (1.3 ml) and the resulting mixture was allowed to warm to 0° C. and diluted with ethyl acetate (150 ml) and brine. After adjusting pH to around 3 with 10% hydrochloric acid, the organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (50 ml) eluting with 15% ethyl acetate in hexane to give (2S)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl- 4-oxo-pyrrolidine (0.54 g).

Aufarbeitung

  1. stirringAfter stirring at -70° C. for 30 minutes, to the mixture
  2. temperatureto warm to 0° C.
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (50 ml)
  8. washeluting with 15% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-30ba85f0573148e7bc7ebb9404c80e31
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081237

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