Aluminium lithium hydride → Tert-butyl 5-(hydroxymethyl)-4-methylthiazol-2-ylcarbamate

HRID 708596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 708596
C[O:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:7][C:6]=1[CH3:18])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:14]([O:13][C:11](=[O:12])[NH:10][C:8]1[S:9][C:5]([CH2:3][OH:2])=[C:6]([CH3:18])[N:7]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 75445982HCID 75445982, Verbindung

Produkt 1

HCID 23560820Tert-butyl 5-(hydroxymethyl)-4-methylthiazol-2-ylcarbamateAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-tert-Butoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid methyl ester (0.5 g) was dissolved in anhydrous THF (7 mL) and cooled to 0° C. and 1 eq of Lithium aluminum hydride (2M solution in THF) was added and stirred 1 h. Reaction was slowly warmed to RT and stirred for 6 h. Reaction was cooled to 0° C. and quenched with min amount of sat. Na2SO4 soln. White solid was filtered and washed with ethyl acetate (5 mL), filtrate was concentrated by rotavap and residue was dired in vacuum gave (5-Hydroxymethyl-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.4 g). This was used in the next reaction without further purification. 1H NMR (400 MHz, Acetone-d6) 4.6 (s, 2H), 2.1 (s, 3H), 1.5 (s, 9H).

Aufarbeitung

  1. customReaction
  2. temperaturewas slowly warmed to RT
  3. stirringstirred for 6 h
  4. customReaction
  5. temperaturewas cooled to 0° C.
  6. customquenched with min amount of sat. Na2SO4 soln
  7. filtrationWhite solid was filtered
  8. washwashed with ethyl acetate (5 mL), filtrate
  9. concentrationwas concentrated by rotavap

Quellen und Nachweise

ORD-Eintrag
ord-76332f5d97b54634b6b57dbe8bfd3a0b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175003B2

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