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Imidazole → 1-(tert-Butyl) 2-methyl (2R,4R)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

HRID 908448
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 908448
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH: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.N1C=CN=C1>CN(C=O)C>[C:4]([Si:1]([CH3:3])([CH3:2])[O:9][C@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1)([CH3:7])([CH3:6])[CH3:5]
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Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Produkt 1

HCID 141170031-(tert-Butyl) 2-methyl (2R,4R)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylateAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Tert-Butyldimethylsilylchloride (9.36 g) was added to a mixture of O1-tert-butyl O2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (13.83 g) and imidazole (9.61 g) in DMF (100 ml). The reaction was stirred at 20° C. for 19 hours and then evaporated to dryness. The residues were slurried in diethyl ether and filtered. The filtrate was evaporated to dryness and the residues purified by flash chromatography on silica eluting with increasingly polar mixtures of methanol/dichloromethane (0/100-5/95). Fractions containing the desired product were combined and evaporated to dryness to give O1-tert-butyl O2-methyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxypyrrolidine-1,2-dicarboxylate (10.35 g) as a colourless oil. NMR Spectrum: (DMSOd6) 0.00 (6H, s); 0.80 (9H, s); 1.32-1.38 (9H, m); 1.84-1.89 (1H, m); 2.30-2.35 (1H, m); 3.06-3.10 (1H, m); 3.49 (1H, q); 3.59 (3H, d); 4.22-4.26 (1H, m); 4.37 (1H, d).

Aufarbeitung

  1. customevaporated to dryness
  2. filtrationfiltered
  3. customThe filtrate was evaporated to dryness
  4. customthe residues purified by flash chromatography on silica eluting
  5. temperaturewith increasingly polar mixtures of methanol/dichloromethane (0/100-5/95)
  6. additionFractions containing the desired product
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b983c52ee7f1441f99f8184f294ddef7
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08017611B2

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