Pyridine, hydrofluoride (1:1) → 4-[(R)-2-Hydroxy-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

HRID 1917283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917283
N1C=CC=CC=1.F.[CH3:8][O:9][C:10]([CH:12]1[CH:16]([C@@H:17]([CH3:27])[CH2:18][O:19][Si](C(C)(C)C)(C)C)[CH2:15][N:14]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:13]1)=[O:11]>N1C=CC=CC=1>[CH3:8][O:9][C:10]([CH:12]1[CH:16]([C@@H:17]([CH3:27])[CH2:18][OH:19])[CH2:15][N:14]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:13]1)=[O:11]

Komponenten

4

Edukt 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 674907934-[(R)-2-(tert-Butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

Produkt 1

HCID 674908004-[(R)-2-Hydroxy-1-(methyl)ethyl]pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl esterAusbeute 179,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Hydrogen fluoride-pyridine (4 mL) was added to a solution of 4-[(R)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]-pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester (6.0 g, 7.1 mmol) in pyridine (20 mL) under ice-cooling, and the mixture was stirred at room temperature for 13 hours. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate and washing with 1N hydrochloric acid and brine. After drying over magnesium sulfate and filtration, the solvent was evaporated under reduced pressure to give 4.1 g (93%) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with 1N hydrochloric acid and brine
  4. dry with materialAfter drying over magnesium sulfate and filtration
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1f893a2356254c838d6c87a68aa8277d
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618094B2

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