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Aluminium lithium hydride → 2,6-Di-tert-butyl-4-[1-(5-hydroxymethyl-1H-imidazole-2-sulfonyl)-piperidin-4-ylsulfanyl]-phenol

HRID 599479
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Reaktionsgleichung

Reaktionsgleichung von HRID 599479
C([O:3][C:4]([C:6]1[NH:7][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([S:20][C:21]3[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=3)[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[N:9][CH:10]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:27]([C:25]1[CH:26]=[C:21]([S:20][CH:17]2[CH2:16][CH2:15][N:14]([S:11]([C:8]3[NH:7][C:6]([CH2:4][OH:3])=[CH:10][N:9]=3)(=[O:13])=[O:12])[CH2:19][CH2:18]2)[CH:22]=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]=1[OH:31])([CH3:30])([CH3:29])[CH3:28]
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Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 866354322-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-3H-imidazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 251680162,6-Di-tert-butyl-4-[1-(5-hydroxymethyl-1H-imidazole-2-sulfonyl)-piperidin-4-ylsulfanyl]-phenolAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-3H-imid-azole-4-carboxylic acid ethyl ester (Ex. 8b, 190 mg, 0.36 mmol) in 3 mL of THF was added 1 mL of 1 M LiAlH4 solution (1 mmol). The reaction was stirred at room temperature for 1 h and then quenched with saturated NaH2PO4 (20 mL). The mixture was diluted with 30 mL of Ethyl acetate and stirred for 10 min and let sit for 1 h. The layers were separated and the aqueous layer was extracted with Ethyl acetate (30 mL). The combined organic phase was dried over Na2SO4 and concentrated under reduced pressure. Chromatography (1-8% Methanol/dichloromethane) gave the title compound as a white solid (125 mg, 72%), mp 122-123° C. 1H NMR (400 MHz, CDCl3): δ 7.23 (s, 2H), 7.07 (s, 1H), 5.29 (s, 1H), 4.65 (s, 2H), 3.72 (m, 2H), 2.88-2.81 (m, 3H), 1.97 (m, 2H), 1.64 (m, 2H), 1.41 (s, 18H). ESI/CI-MS m/z 482 ([M+H]+), 480 ([M−H]−). Two HPLC (reverse-phase, C, 8) methods were used to determine the purity of the title compound. Method 1: gradient elution, 60% to 85% solvent B (A=aqueous 0.1% H3PO4, B=MeCN) in 15 min. Purity (UV-VIS): 98.3% (238 nm); Method 2: gradient elution, 40% to 95% solvent B (A=10 mM NH4OAc, B=MeCN) in 6 min. Purity (UV-VIS λ): 98.5% (215 nm), 99.5% (254 nm), 99.5% (280 nm).

Aufarbeitung

  1. customquenched with saturated NaH2PO4 (20 mL)
  2. additionThe mixture was diluted with 30 mL of Ethyl acetate
  3. stirringstirred for 10 min
  4. waitlet sit for 1 h
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with Ethyl acetate (30 mL)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-98a6e14add204e7f8c7a6e3f7ac8dea6
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897776B2

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