Isobutylene → HCID 19095414, compound

HRID 486588Notes

Reaction equation

HRID 486588 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[CH3:5][C:6]1[C:11]2=[CH:12][C:13]3[CH2:14][CH2:15][C:16]4[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:17]=4[C:18]=3[N:10]2[CH2:9][CH2:8][N:7]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+].[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38]>C(Cl)Cl.C(O)C.CO>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]/[C:37]([OH:39])=[O:38].[C:2]([O:23][C:21]1[CH:20]=[CH:19][C:17]2[C:18]3[N:10]4[CH2:9][CH2:8][N:7]=[C:6]([CH3:5])[C:11]4=[CH:12][C:13]=3[CH2:14][CH2:15][C:16]=2[CH:22]=1)([CH3:3])([CH3:1])[CH3:4]

Participants

9

Reactant 5

HCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 444972Fumaric AcidHCID 135736931HCID 135736931, compound

Product 1

HCID 19095414HCID 19095414, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Isobutylene (11.0 g) was condensed under argon into a solution of 1.0 g of 5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indol-3-ol in 50 ml of methylene chloride. The solution was cooled to -78° C. and treated with 0.4 ml of trifluoromethanesulphonic acid while stirring. The mixture was stirred at -78° C. for 8 hours and at -5° C. for 30 minutes. Subsequently, 50 ml of methanol were added and the mixture was neutralized with powdered sodium hydroxide. The reaction mixture was freed from solvent and chromatographed over 100 g of aluminium oxide (neutral, III) with methylene chloride as the eluent. The crude product, 0.3 g of yellow oil, was dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. The solution was concentrated to half and treated with 5 ml of ethyl acetate. There was obtained 0.11 g (6%) of 3-tert-butoxy-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 179°-181° C. (dec.).

Workup

  1. stirringThe mixture was stirred at -78° C. for 8 hours and at -5° C. for 30 minutes
  2. customchromatographed over 100 g of aluminium oxide (neutral, III) with methylene chloride as the eluent
  3. dissolutionThe crude product, 0.3 g of yellow oil, was dissolved in a 20-fold amount of ethanol
  4. concentrationThe solution was concentrated to half
  5. additiontreated with 5 ml of ethyl acetate

Sources & evidence

ORD record
ord-c8f2f15e3a0a4a008e5fdd0a1507b09d
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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