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

HRID 1195070Notes

Reaction equation

HRID 1195070 reaction equation
C[Si](C)(C)[Br:3].[OH:6][CH2:7][C@@H:8]1[CH:23]=[C: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)[N:10]([CH3:11])[CH2:9]1.N>CS(C)=O>[Br:3][C:15]1[NH:16][C:17]2[C:24]3[C:14]=1[CH2:13][C@@H:12]1[C:22]([C:21]=3[CH:20]=[CH:19][CH:18]=2)=[CH:23][C@@H:8]([CH2:7][OH:6])[CH2:9][N:10]1[CH3:11]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 149871413-67-8HCID 76113Bromotrimethylsilane

Product 1

HCID 181032Ergoline-8-methanol, 2-bromo-9,10-didehydro-6-methyl-, (8beta)-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

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%),

Workup

  1. additionis added
  2. stirringAfter stirring for 20 minutes
  3. extractionThe mixture is extracted 3 times with 30 ml of dichloromethane each
  4. washThe combined organic phase is washed 3 times with 20 ml of 10% sodium chloride solution each,
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4f4a099ce5a64123bfdab861ebda4d61
Source dataset
uspto-grants-1989_03
Patent number
US04816587

Reaction notes

Loading…