Diazomethane → HCID 21912816, Verbindung
Reaktionsgleichung
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][NH:17][C:16](=[O:19])[C:15]=2[CH3:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:23])=[N-]>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][N:17]=[C:16]([O:19][CH3:23])[C:15]=2[CH3:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A suspension of 1-tert-butoxycarbonyl-4-(4-methyl-(1H)-pyrazol-3-one-5-yl)piperidine (from Step C) in 12.5 mL (9.9 mmol) of 0.8 M diazomethane in Et2O was allowed to stand (occasional swirling) until all solids were in solution. Excess diazomethane was quenched with HOAc. The reaction was partitioned between 1 N NaHCO3 and Et2O. After separating phases, the organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography using 19:1 v/v hexanes/acetone, 9:1 v/v hexanes/acetone and 4:1 v/v hexanes/acetone as the gradient to afford the title compound as a yellow oil: RF: 0.18 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.48 (s, 9H), 1.57–1.65 (m, 2H), 1.82–1.85 (m, 2H), 1.89 (s, 3H), 2.70–2.79 (m, 3H), 3.91 (s, 3H), 4.24 (m, 2H)-; 13C-NMR (125 MHz) δ 55.7 (O—CH3).