Sodium Carbonate → Benzyl (4-hydroxy-2-methylbutan-2-yl)carbamate

HRID 1056354

Reaktionsgleichung

Reaktionsgleichung von HRID 1056354
[NH2:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].C([O-])([O-])=O.[Na+].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>>[CH2:18]([O:17][C:15](=[O:16])[NH:1][C:2]([CH3:7])([CH2:3][CH2:4][OH:5])[CH3:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 6410003-Amino-3-methylbutan-1-ol

Produkt 1

HCID 15473339Benzyl (4-hydroxy-2-methylbutan-2-yl)carbamateAusbeute 72,4 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 150-mL round-bottomed flask was added 3-amino-3-methyl-butan-1-ol (2.18 mL, 19.39 mmol, Tyger Sci. Inc) and Na2CO3 (3.08 g, 29.1 mmol) (1 M in water) and the solution was cooled to 0° C. Benzyl chloroformate (3.03 mL, 21.33 mmol, Sigma-Aldrich) was added dropwise and the mixture was stirred at 0° C. for 2 h. The mixture was extracted with EtOAc (100 mL×3) and the combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified with silica gel chromatography (eluted with 10-50% EtOAc in Hex) to give benzyl(4-hydroxy-2-methylbutan-2-yl)carbamate (3.33 g, 14.03 mmol, 72% yield) as a clear oil. MS (ESI, pos. ion) m/z: 238.1 (M+1).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (100 mL×3)
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified with silica gel chromatography (eluted with 10-50% EtOAc in Hex)

Quellen und Nachweise

ORD-Eintrag
ord-d953c7ede58d44a188dda5caff5d741c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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