Tetrahydrofuran → (-)(2aR,4S)-6-(2-furyl)-4-(di-n-propylamino)-1,2,2a,3,4,5hexahyrobenz[cd]indole

HRID 2257217Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.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)C1OC=CC=1)CCC>C(OCC)(=O)C.CCCCCC.[OH-].[NH4+].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>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]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]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])[CH2:24][C:18]=1[C:17]=23

Participants

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 eluent gave the protected analog of the title compound in 61% yield.

Workup

customcap
waitAfter 24 hours
temperaturethe reaction mixture was cooled
filtrationfiltered through a celite pad
concentrationthe resulting filtrate was then concentrated in vacuo
customto provide a viscous orange oil

Sources & evidence

ORD record: ord-845a963694534353933eed0802cedc0f
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05656653

Reaction notes

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