Tetrahydrofuran → tert-Butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate

Reaktionsgleichung

C([Mg]Cl)(C)C.[C:6]([O:10][C:11](=[O:25])[NH:12][C:13]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]#N)=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].[CH2:26]([Mg]Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C[O:38]CC1>>[C:6]([O:10][C:11](=[O:25])[NH:12][C:13]1([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:38])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7]

Komponenten

Edukt 4

HCID 8028Tetrahydrofuran3×

HCID 46856381tert-Butyl [1-(4-cyanophenyl)cyclobutyl]carbamate

HCID 178418336HCID 178418336, Verbindung

HCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 57805516tert-Butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate

Versuchsvorschrift

A solution of i-PrMgCl (9.65 mL, 19.3 mmol) in THF was added dropwise to a solution of compound 1-2 (5.24 g, 19.3 mmol) in dry THF at −5.deg.C. After stirring for 20 min, a solution of BnMgCl (29 mL, 2M, 58 mmol) in THF was added dropwise to the reaction mixture. After completion of addition, the reaction mixture was stirred for 1 h at 0.deg.C, then warmed slowly to room temperature, and stirred for another 1 h. The reaction was quenched with saturated NH4 Cl solution, extracted with ethyl acetate. Separated and collected the organic layer, and the aqueous solution was washed EA for two times. The combined organic layer was washed with brine, dried and concentrated in vacuo to get the crude product, which was purified by silica chromatography to give 5.5 g of ketone 1-3.