(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester → (S)-1-(2,6-dimethyl-phenyl)-3-isobutyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

HRID 1020987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020987
[CH3:1][O:2][C:3]([C@@:5]1([CH2:19][C:20]([CH3:22])=[CH2:21])[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH2:6]1)=[O:4]>CO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([C@@:5]1([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:9][C:8](=[O:10])[N:7]([C:11]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:18])[CH2:6]1)=[O:4]

Komponenten

5

Edukt 1

HCID 58218819(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Produkt 1

HCID 58218845(S)-1-(2,6-dimethyl-phenyl)-3-isobutyl-5-oxo-pyrrolidine-3-carboxylic acid methyl esterAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

10% Pd/C (120 mg) was added to a solution of (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (prepared from step d, 474 mg, 1.57 mmol) in MeOH (5 mL) and resulting black suspension was stirred at room temperature overnight under H2 gas using a balloon. The reaction mixture was then diluted with EtOAc (25 mL) and filtered through celite, washed with MeOH (25 mL) and volatiles from filtrate were evaporated to obtain crude product which was purified by flash chromatography (SiO2, 20→60% EtOAc/hexanes) to obtain (S)-1-(2,6-dimethyl-phenyl)-3-isobutyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (450 mg, 94% yield). LC-MS: Rt (retention time): 2.55 min, MS: (ES) m/z 304.1 (M+H+).

Aufarbeitung

  1. customresulting black suspension
  2. filtrationfiltered through celite
  3. washwashed with MeOH (25 mL) and volatiles from filtrate
  4. customwere evaporated
  5. customto obtain crude product which
  6. customwas purified by flash chromatography (SiO2, 20→60% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-11c0a1ff412549cba929a11da3ea795c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716494B2

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