Dimethylformamide → HCID 18654743, compound

HRID 1289897Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:6][C@@H:5]3[CH2:30][C@H:31]([N:33]([CH2:37][CH2:38][CH3:39])[CH2:34][CH2:35][CH3:36])[CH2:32][C:3]=1[C:4]=23.C([Li])CCC.CN(C)[CH:47]=[O:48]>O1CCCC1.CCCCCC>[CH:47]([C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:6][C@@H:5]3[CH2:30][C@H:31]([N:33]([CH2:37][CH2:38][CH3:39])[CH2:34][CH2:35][CH3:36])[CH2:32][C:3]=1[C:4]=23)=[O:48]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (-)(2aR,4S)-6-bromo-1-trityl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (6.8 g, 12 mmol) in 100 ml of tetrahydrofuran cooled to -78° C. under a nitrogen atmosphere was added dropwise a 1.6M solution of n-butyllithium in hexane. The reaction mixture was stirred at -78° C. for 1 hour. Dimethylformamide (3 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was quenched with water and then extracted with ethyl acetate. The ethyl acetate solution was washed with a saturated brine solution, dried over magnesium sulfate and concentrated to dryness to provide 5.6 g of the above-titled compound as an oil.

Workup

stirringthe mixture was stirred at room temperature for 30 minutes
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
washThe ethyl acetate solution was washed with a saturated brine solution
dry with materialdried over magnesium sulfate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-049e35ba190d4747a7121f4f0e861a13
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750554

Reaction notes

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