Tetrabutylammonium Fluoride → HCID 67085592, compound

HRID 2036750Notes

Reaction equation

HRID 2036750 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15](COCC[Si](C)(C)C)[C:14]4[CH2:27][CH:28]5[NH:32][CH:31]([C:13]=4[C:12]=3[C:11]=2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[NH:15][C:14]4[CH2:27][CH:28]5[NH:32][CH:31]([C:13]=4[C:12]=3[C:11]=2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][CH2:29]5)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131731027HCID 131731027, compound

Product 1

HCID 67085592HCID 67085592, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of step B (1.28 g, 2.25 mmol) in THF (30 mL) was added a 1M solution of TBAF in THF (12 mL, 12.0 mmol) and the resulting solution heated to reflux overnight. The reaction was concentrated in vacuo to a reduced volume and diluted with a saturated aqueous solution of ammonium chloride followed by water. The mixture was extracted with dichloromethane and the organic phase dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 4:1 to 1:1 hexane/ethyl acetate) to give tert-butyl 2-phenylsulfonyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole-carboxylate (0.91 g, 93%) as a white foam: 1H NMR (CD3OD, 300 MHz) δ 8.12 (s, 1H), 7.91-7.96 (m, 2H), 7.48-7.62 (m, 4H), 7.41 (d, J=8.7 Hz, 1H), 5.19-5.28 (m, 1H), 4.52-4.61 (m, 1H), 3.35-3.48 (m, 1H), 2.58 (d, J=16.2 Hz, 1H), 2.15-2.41 (m, 2H), 1.90-1.99 (m, 1H), 1.64-1.75 (m, 1H), 1.27-1.49 (m, 9H).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction was concentrated in vacuo to a reduced volume
  4. additiondiluted with a saturated aqueous solution of ammonium chloride
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialthe organic phase dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (SiO2, 4:1 to 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-95151aaffd344acdafaaf5b00d6a70e6
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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