Water → (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 846920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846920
[C:1]([C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])(=[O:3])[CH3:2].C1C=C[NH+]=CC=1.[Br:33][Br-]Br.O.C(OCC)(=O)C>O1CCCC1>[Br:33][CH2:2][C:1]([C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:11])=[O:12])[CH2:6][N:5]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)=[O:15])=[O:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57232963(2S,4R)-2-acetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2S,4R)-2-acetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.5 g) in tetrahydrofuran (80 ml) was added pyridinium bromide perbromide (2.59 g) at 5°-10° C. After stirring at room temperature for 3 hours, the mixture was poured into water (80 ml) and ethyl acetate (160 ml). The separated organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and brine successively dried over magnesium sulfate, and evaporated in vacuo. The oily residue was subjected to a column chromatography on silica gel (60 g) eluting with a mixture of acetone and dichloromethane (1:20 V/V) to give (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.98 g).

Aufarbeitung

  1. washThe separated organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialsuccessively dried over magnesium sulfate
  3. customevaporated in vacuo
  4. washeluting with a mixture of acetone and dichloromethane (1:20 V/V)

Quellen und Nachweise

ORD-Eintrag
ord-2230f8cc16ee400e928e5ad11bddaf6e
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05138064

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