[CH2:1]([Si:3](Cl)([CH2:6]C)[CH2:4]C)C.[OH:9][CH2:10][C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][CH:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH2:18]3)[N:13]([CH3:14])[CH2:12]1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.CN(C)C=O>[CH3:6][Si:3]([CH3:1])([CH3:4])[O:9][CH2:10][C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:13]([CH3:14])[CH2:12]1Triethylsilyl chloride (TES-Cl, 1.30 g) is added into a mixture of dihydrolysergol (1.47 g), triethylamine (1.74 g) and DMAP (0.14 g) in N,N-dimethylformamide (10 mL) and the mixture is stirred at room temperature. After complete reaction, the mixture is cooled and water (15 mL) is added. The resulted suspension is stirred for an additional 2 h and then filtered and washed with water. The product is dried and recrystallized from dichloromethane/heptanes to give 1.47 g of 8β-(trimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline in 70% yield.
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