tert-Butanol → tert-Butyl cyclohex-3-en-1-ylcarbamate

Reaktionsgleichung

[CH:1]1(C(O)=O)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[C:34]([OH:38])([CH3:37])([CH3:36])[CH3:35]>>[CH:1]1([NH:12][C:15](=[O:24])[O:38][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Komponenten

Edukt 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 209033-Cyclohexene-1-carboxylic acid

HCID 199401P,P-Diphenylphosphinic azide

Produkt 1

HCID 11063381tert-Butyl cyclohex-3-en-1-ylcarbamate

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

3-Cyclohexene-1-carboxylic acid (25.3 g) was dissolved in tert-butanol (250 ml), triethylamine (28 ml) and diphenylphosphorylazide (43.0 ml) were added, and the mixture was stirred for 1 hour at room temperature and 2 days at 90° C. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methylene chloride) and then repurified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to obtain the title compound (24.9 g).