Hydrochloric Acid → Cis-4b,5,9b,10-tetrahydro-8-methoxy-6,7,9-trimethylindeno[1,2-b]indole

HRID 439875Notes

Reaction equation

HRID 439875 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]2[NH:8][C:7]3[C:14]4[C:19]([CH2:20][C:6]=3[C:5]=2[C:4]=1[CH3:21])=[CH:18][CH:17]=[CH:16][CH:15]=4.O1CCN(B)CC1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]([CH3:13])[C:9]2[NH:8][C@@H:7]3[C:14]4[C:19]([CH2:20][C@@H:6]3[C:5]=2[C:4]=1[CH3:21])=[CH:18][CH:17]=[CH:16][CH:15]=4

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5028646HCID 5028646, compoundHCID 22408509HCID 22408509, compound

Product 1

HCID 57275855Cis-4b,5,9b,10-tetrahydro-8-methoxy-6,7,9-trimethylindeno[1,2-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.65 g (0.00234 mol) of 5,10-dihydro-8-methoxy-6,7,9-trimethylindeno[1,2-b]indole and 0.95 g (0.00957 mol) of morpholino borane in 4 ml of dioxane was added dropwise 1 ml of concentrated hydrochloric acid. The mixture was refluxed for 30 minutes, cooled to room temperature whereupon 3 ml of 6N hydrochloric acid was added. The mixture was then refluxed for another 30 minutes. After cooling to room temperature, the crude mixture was partitioned between ether and aqueous sodium hydroxide. The organic phase was separated and washed with aqueous sodium hydroxide and with water. Drying (MgSO4) and evaporation gave the crude product which was recrystallized from ethyl acetate/light petroleum. Yield 0.46 g (70%). 1H NMR (CDCl3): 2.0 (3H,s), 2.14 (3H,s), 2.28 (3H,s), 3.17 (1H,dd), 3.55 (1H,dd), 3.64 (1H,s), 4.28 (1H,ddd), 5.38 (1H,d), 7.20-7.27 (3H,m), 7.39 (1H,d).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. additionwas added
  3. temperatureThe mixture was then refluxed for another 30 minutes
  4. customthe crude mixture was partitioned between ether and aqueous sodium hydroxide
  5. customThe organic phase was separated
  6. washwashed with aqueous sodium hydroxide and with water
  7. customDrying
  8. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-926ec8b2df3a480d9d10c74074bd20bf
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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