Imidazole → (R)-t-Butyl 2-((t-butyldimethylsilyloxy)methyl)piperazine-1-carboxylate

HRID 79188

Reaktionsgleichung

Reaktionsgleichung von HRID 79188
[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Si:20]([O:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 24820219(R)-2-Hydroxymethyl-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 58299667(R)-t-Butyl 2-((t-butyldimethylsilyloxy)methyl)piperazine-1-carboxylateAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-t-Butyl 2-(hydroxymethyl)piperazine-1-carboxylate (1.15 g, 5.32 mmol), t-butylchlorodimethylsilane (0.882 g, 5.85 mmol), and imidazole (0.796 g, 11.7 mmol) were stirred in dichloromethane (3 mL) for three days. The solution was added to aqueous K2CO3 (30 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give a yellow oil. Silica gel chromatography (gradient elution hexanes/0-50% ethyl acetate) afforded compound 308 as a colorless oil (1.06 g, 60%).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil
  5. washSilica gel chromatography (gradient elution hexanes/0-50% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-57b2c2a245a64c9493a362b4fa19c332
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841312B2

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