tert-Butanol → Ethyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate

Reaktionsgleichung

C([N:3]([CH2:6]C)CC)C.[CH2:8]([O:10][C:11]([C:13]1(C(O)=O)[CH2:15][CH2:14]1)=[O:12])[CH3:9].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>>[CH2:8]([O:10][C:11]([C:13]1([NH:3][C:6]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:26])[CH2:14][CH2:15]1)=[O:12])[CH3:9]

Komponenten

Edukt 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

Produkt 1

HCID 10242916Ethyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylateAusbeute 91 %

Versuchsvorschrift

Triethylamine (29.82 mL, 214 mmol) was added under nitrogen dropwise to a mixture of 1,1-cyclopropanedicarboxylic acid monoethyl ester (31.518 g, 199 mmol), prepared in the previous step, and diphenylphosphoryl azide (47.4 mL, 219 mmol) in 40 mL of tert-butanol at room temperature. After the addition, the reaction was refluxed for 5 h. The reaction was concentrated under reduced pressure. The residue was taken up in ethyl acetate and extracted three times each with 5% citric acid, saturated NaHCO3 and saturated NaCl. The ethyl acetate layer was dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give 1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropane carboxylic acid ethyl ester (41.3931 g, 91%) as a yellow oil, MS (ES) m/z 130.0 [M+H-tBoc].