Cesium carbonate → 2-((1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41580Notes

Reaction equation

HRID 41580 reaction equation
S([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][C:23]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:22]2=[O:32])=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][C:23]3([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:22]2=[O:32])=[CH:12]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 672515122-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one

Product 1

HCID 672520892-((1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-oneYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of 2-((1-tosyl-1H-indol-3-yl)methyl)-2,9-diazaspiro[5.5]undecan-1-one (15 g, 23 mmol) and Cs2CO3 (45 g, 139 mmol) in methanol (170 ml) was heated under reflux for 2.5 h. The solution was diluted with water, the pH adjusted to 7 with a saturated aqueous potassium carbonate solution and the aqueous phase extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 6.69 g (99%) of the title compound as a beige foam which was not further purified. [1H NMR (400 MHz, DMSO-d6) ♀ ppm 10.91 (br. s., 1H), 7.48-7.55 (m, 1H), 7.32 (d, J=8.2 Hz, 1H), 7.24 (d, J=2.0 Hz, 1H), 7.04 (t, J=7.6 Hz, 1H), 6.88-6.96 (m, 1H), 4.60 (s, 2H), 3.10 (t, J=6.1 Hz, 2H), 2.71-2.89 (m, 2H), 2.51-2.69 (m, 2H), 2.01 (s, 3H), 1.54-1.73 (m, 4H), 1.25-1.38 (m, 2H); LCMS RtC=2.44 min, [M+H]+=298.2].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 h
  3. extractionthe aqueous phase extracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-867b688985e44edba8bc198270e19de8
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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