Tetrahydrofuran → Ammonium Hydroxide

HRID 55338Notes

Reaction equation

HRID 55338 reaction equation
[O:1]1CCCC1.C([N:14]1[C:22]2[CH:21]=[CH:20][C:19](I)=[C:18]3[CH2:24][C@@H:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])[CH2:26][C@H:16]([C:17]=23)[CH2:15]1)(=O)C1C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:39]1[O:40][CH:41]=[CH:42][CH:43]=1)CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[OH-:1].[NH4+:14].[O:40]1[CH:41]=[CH:42][CH:43]=[C:39]1[C:19]1[CH:20]=[CH:21][C:22]2[NH:14][CH2:15][C@@H:16]3[CH2:26][C@H:25]([N:27]([CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH3:33])[CH2:24][C:18]=1[C:17]=23

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 43936882-(Tributylstannyl)furanHCID 9805495(+)(2aR,4S)-l-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Product 2

HCID 14923Ammonium HydroxideYield 0.5%HCID 15221121(-)(2aR,4S)-6-(2-furyl)-4-(di-n-propylamino)-1,2,2a,3,4,5hexahyrobenz[cd]indole

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
100 °C

Procedure

To a sealable tube with threads containing 13 ml of dry tetrahydrofuran were added 1.2 g (2.46 mmol) of (+)(2aR,4S)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole, 968 mg (2.71 mmol) of 2-(tributylstannyl)furan and 200 mg of bis(triphenylphosphine)palladium(II) chloride. The resulting mixture was then deaerated with argon for 15 minutes. After deaeration, the tube was sealed with a teflon cap and the contents thereof were heated to 100° C. for 24 hours. After 24 hours, the reaction mixture was cooled, filtered through a celite pad and the resulting filtrate was then concentrated in vacuo to provide a viscous orange oil. Flash chromatography of this oil over silica gel with 60% ethyl acetate/hexane plus 0.5% ammonium hydroxide as gave the protected analog of the title compound in 61% yield.

Workup

  1. customcap
  2. waitAfter 24 hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered through a celite pad
  5. concentrationthe resulting filtrate was then concentrated in vacuo
  6. customto provide a viscous orange oil

Sources & evidence

ORD record
ord-f4ded028e16d4905a401c60350d12e14
Source dataset
uspto-grants-1997_04
Patent number
US05624944

Reaction notes

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