tert-Butanol → tert-Butyl (3-isobutylcyclobutyl)carbamate

HRID 1912101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912101
[CH2:1]([CH:5]1[CH2:8][CH:7](C(O)=O)[CH2:6]1)[CH:2]([CH3:4])[CH3:3].[C:12]([OH:16])([CH3:15])([CH3:14])[CH3:13].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C>>[CH2:1]([CH:5]1[CH2:6][CH:7]([NH:36][C:39](=[O:24])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8]1)[CH:2]([CH3:3])[CH3:4]

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 83635449cis-3-Isobutylcyclobutane carboxylic acid

Produkt 1

HCID 71135570tert-Butyl (3-isobutylcyclobutyl)carbamate

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

3-Isobutylcyclobutanecarboxylic acid (3.00 g) and tert-butanol (30 mL) were mixed. To the mixture were added triethylamine (4.28 mL) and diphenylphosphoryl azide (5.38 mL) at ice temperature. After stirring at 95° C. overnight, the reaction mixture was concentrated in vacuo. To the resultant residue was added ethyl acetate. The mixture was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/40) to give the title compound (2.91 g).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionTo the resultant residue was added ethyl acetate
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/40)

Quellen und Nachweise

ORD-Eintrag
ord-38a14eaa31c44156ae991e30b708c2db
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604069B2

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