Ammonia → Ergoline-8-methanol, 2-bromo-9,10-didehydro-6-methyl-, (8beta)-

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Reaction Steps

2 g of trimethylbromosilane are portionwise added to 20 ml of dimethylsulfoxide and the reaction mixture is stirred at room temperature for 15 minutes, then a solution containing 1 g of lysergol in 15 ml of dimethylsulfoxide is added. After stirring for 20 minutes, the mixture is poured onto 150 ml of ice-water and the pH is adjusted to 8-9 by adding aqueous ammonia. The mixture is extracted 3 times with 30 ml of dichloromethane each. The combined organic phase is washed 3 times with 20 ml of 10% sodium chloride solution each, dried over sodium sulfate, filtered and the filtrate is evaporated under reduced pressure to give the title compound in a yield of 0.8 g (0.00277 mole, 70.5%),

Provenance & Evidence