Potassium Carbonate → N-Boc-cis-4-hydroxy-L-proline methyl ester

HRID 257961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257961
C([O:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[C:18]([O:17][C:15]([N:13]1[CH2:14][C@@H:10]([OH:9])[CH2:11][C@H:12]1[C:22]([O:24][CH3:25])=[O:23])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 10760219(2S,4S)-1-tert-Butyl 2-methyl 4-(benzoyloxy)pyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,4S)-4-benzoyloxy-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine (30.0 g) in methanol (600 ml) was added potassium carbonate (11.9 g) and the mixture was stirred at room temperature for 1 hour. The solution was diluted with ethyl acetate (1 l) and washed with water. The organic phase was washed with brine. The aqueous phase was saturated with sodium chloride, extracted with chloroform and washed with brine. The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to give an oil. The oil was chromatographed on a silica gel (500 g) column with a mixture of n-hexane and ethyl acetate (1:1) as an eluent to give (2S,4S)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine (20.7 g) as colorless crystal.

Aufarbeitung

  1. washwashed with water
  2. washThe organic phase was washed with brine
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give an oil
  8. customThe oil was chromatographed on a silica gel (500 g) column with a mixture of n-hexane and ethyl acetate (1:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-052434921f5e4e4abc31ba9e39eb5010
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264453

Notizen zur Reaktion

Wird geladen…