Diisobutylaluminum hydride → Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

HRID 2356054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356054
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18](OC)=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:19][CH2:18][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

Produkt 1

HCID 13969831Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of Example 175A (1.22 g, 3.91 mmol) in toluene (10 mL) at −78° C. was treated with 1M DIBAL-H in toluene (8.6 mL), warmed to room temperature over 4 hours, diluted with ethyl acetate (100 mL), washed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 284 (M+H)+.

Aufarbeitung

  1. washwashed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2cb0fdec93634e24a7a76c6d82e22a9e
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754886B2

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