Imidazole → (S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amine

HRID 2091532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091532
[NH2:1][C@@H:2]([CH3:7])[C:3]([CH3:6])([OH:5])[CH3:4].N1C=CN=C1.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:17]([O:5][C:3]([CH3:6])([CH3:4])[C@@H:2]([NH2:1])[CH3:7])([C:14]([CH3:16])([CH3:15])[CH3:13])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 51415372(S)-3-Amino-2-methylbutan-2-OL

Produkt 1

HCID 58485259(S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-3-amino-2-methylbutan-2-ol (4 g, 38.8 mmol) and imidazole (5.20 g, 77.7 mmol) in CH2Cl2 (50 mL) was added TBSCl (8.7 g, 57.7 mmol) at 0° C. The mixture was stirred overnight. The mixture was washed with brine. The organic phase was separated and concentrated to give (S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amine (8.4 g, 100%), which was used for the next step without purification. 1H NMR (CDCl3): 0.00 (s, 6H), 0.73 (s, 9H), 1.08 (s, 3H), 1.12 (d, 3H), 1.21 (s, 3H), 2.83 (q, 1H), 4.08 (brs, 1H).

Aufarbeitung

  1. washThe mixture was washed with brine
  2. customThe organic phase was separated
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-635931ada7f84e98ba858ce93cf2ee83
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440658B2

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