Tetrahydrofuran → benzyl (2R,4R)-4-hydroxy-2-methoxy-methyl-carbamoyl-pyrrolidine-1-carboxylate

HRID 13433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 13433
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C@@H:27]([C:40](=[O:45])[N:41](OC)C)[CH2:26]1)(C)(C)C.[O:58]1CCC[CH2:59]1>>[OH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C@@:27]([C:40](=[O:45])[NH2:41])([O:58][CH3:59])[CH:26]1[CH3:2]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86619216benzyl (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylate

Produkt 1

HCID 86619217benzyl (2R,4R)-4-hydroxy-2-methoxy-methyl-carbamoyl-pyrrolidine-1-carboxylate

Versuchsvorschrift

7.46 ml of tetrabutylammonium fluoride (1 M tetrahydrofuran solution) was added to a tetrahydrofuran (30 ml) solution of 2.04 g of benzyl (2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylate obtained in (step 2), and the reaction liquid was stirred at room temperature for 20 minutes. The solvent of the reaction liquid was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/3) to obtain the entitled compound.

Aufarbeitung

  1. customobtained in (step 2)
  2. customthe reaction liquid
  3. customThe solvent of the reaction liquid
  4. customwas evaporated away under reduced pressure
  5. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/3)
  6. customto obtain the entitled compound

Quellen und Nachweise

ORD-Eintrag
ord-e7d48644d4c84c7a8f0afdd95ac4e7e9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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