Acetone → Acetoneberberine

반응식

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][N+:7]3[CH2:20][CH2:19][C:18]4[C:13](=[CH:14][C:15]5[O:23][CH2:22][O:21][C:16]=5[CH:17]=4)[C:8]=3[CH:9]=2)[C:4]=1[O:24][CH3:25].[Cl-].O.[OH-].[Na+].[CH3:30][C:31]([CH3:33])=[O:32]>>[CH3:25][O:24][C:4]1[C:5]2[CH:6]([CH2:30][C:31](=[O:32])[CH3:33])[N:7]3[CH2:20][CH2:19][C:18]4[C:13]([C:8]3=[CH:9][C:10]=2[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])=[CH:14][C:15]1[O:23][CH2:22][O:21][C:16]=1[CH:17]=4

참가 물질

반응물 4

HCID 180Acetone

HCID 962Water

HCID 12456Berberine chloride

HCID 14798Sodium Hydroxide

생성물 1

HCID 11728929Acetoneberberine수율 80%

실험 절차

Berberine hydrochloride (10.0 g, 26.90 mmol), water (40 mL), acetone (10 mL), 50% aqueous sodium hydroxide (15 mL) was introduced into a reaction vessel. The reaction mixture was stirred vigorously for 30 min at room temperature. The resulting precipitate was collected and washed with 80% methanol (2×10 mL) and then dried to afford 1-(9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-yl)-propan-2-one (8.5 g, 80%) as a yellow solid. LC/MS m/e calcd for C23H23NO5 (M+H)+: 394.44, observed: 336.0; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.04 (s, 3 H) 2.31 (dd, J=14.65, 4.80 Hz, 1 H) 2.66-2.75 (m, 1 H) 2.75-2.82 (m, 1 H) 2.94 (dd, J=14.65, 6.57 Hz, 1 H) 3.16-3.25 (m, 1 H) 3.25-3.30 (m, 1 H) 3.77 (d, J=2.02 Hz, 6 H) 5.21 (dd, J=6.32, 4.80 Hz, 1 H) 5.97-6.03 (m, 3 H) 6.72 (d, J=8.34 Hz, 1 H) 6.76 (s, 1 H) 6.87 (d, J=8.34 Hz, 1 H) 7.25 (s, 1 H).