Allyl acetate → Cabergoline

反応式

[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][CH2:5][N:6]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])[C:7]([C@@H:9]1[CH2:23][C@H:22]2[C@@H:12]([CH2:13][C:14]3[C:24]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]2=4)[NH:16][CH:15]=3)[NH:11][CH2:10]1)=[O:8].C(O[CH2:35][CH:36]=[CH2:37])(=O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:37]([N:11]1[C@H:12]2[C@@H:22]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]4[C:24]=3[C:14]([CH2:13]2)=[CH:15][NH:16]4)[CH2:23][C@@H:9]([C:7]([N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:30])[C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[O:8])[CH2:10]1)[CH:36]=[CH2:35]

参加物

実験手順

To a suspension of 9.0 g (21.87 mmol) N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl)-ergoline-8β-carboxamide (XIX) in 250 ml of toluene 0.5 g of tetrakis(triphenylphosphine)palladium(0) and 5 ml of allyl acetate was added, and the reaction mixture was stirred at ambient temperature for 2 hours. The resulting mixture was washed with 100 ml of water. The organic layer was dried over anhydrous sodium sulphate. The dried solution was concentrated in vacuum and the product was purified on a silica plug to give 9.1 g (92.3%) of the title compound.