Imidazole → (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

HRID 13431

Reaktionsgleichung

Reaktionsgleichung von HRID 13431
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.CN(C)C=O.[CH2:29]([O:36][C:37]([N:39]1[CH2:43][C@H:42]([OH:44])[CH2:41][C@@H:40]1[C:45]([OH:47])=[O:46])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)(=O)C>[CH2:29]([O:36][C:37]([N:39]1[CH2:43][C@H:42]([O:44][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:41][C@@H:40]1[C:45]([OH:47])=[O:46])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 688416(2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 67482921(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.32 g of tert-butyldiphenylsilyl chloride and 2.32 g of imidazole were added in order to a dimethylformamide (60 ml) solution of 3.61 g of (2R,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, washed with aqueous saturated ammonium chloride and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2) to obtain the entitled compound.

Aufarbeitung

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with aqueous saturated ammonium chloride and saturated saline in order
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/2)
  7. customto obtain the entitled compound

Quellen und Nachweise

ORD-Eintrag
ord-72690fe8b46b401484ce85a4f574b9e7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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