Potassium Carbonate → HCID 66781621, compound

HRID 1095249Notes

Reaction equation

HRID 1095249 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:31][CH2:30][C:25]5([O:29][CH2:28][CH2:27][O:26]5)[CH2:24][CH2:23]4)[CH2:18][CH:17]=3)=[C:12]([F:32])[CH:11]=2)[CH2:6][CH2:5]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[H][H]>C1(C)C=CC=CC=1.C(O)(C)C.[Pd]>[CH2:1]([O:3][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:17][CH2:18][CH:19]([CH:22]4[CH2:31][CH2:30][C:25]5([O:26][CH2:27][CH2:28][O:29]5)[CH2:24][CH2:23]4)[CH2:20][CH2:21]3)=[C:12]([F:32])[CH:11]=2)[CH2:8][CH2:9]1)[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66781461HCID 66781461, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66781621HCID 66781621, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

The compound (24) was dissolved in a mixed solvent of toluene (150 ml) and isopropyl alcohol (150 ml), and then Pd/C (2.35 g) and potassium carbonate (0.40 g) were added thereto. The mixture was stirred at room temperature under a hydrogen atmosphere until hydrogen absorption had ceased. After the reaction had been completed, Pd/C was removed and then the solvent was distilled off. The residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=9:1 by volume) as an eluent and silica gel as a stationary phase powder, and dried, giving 31.4 g of 8-(4-(4-(4-ethoxycyclohexyl)-2-fluorophenyl)cyclohexyl)-1,4-dioxaspiro[4,5]decane (25). The yield based on the compound (24) was 66.4%.

Workup

  1. customPd/C was removed
  2. distillationthe solvent was distilled off
  3. customThe residue was purified with a fractional operation by means of column chromatography
  4. customsilica gel as a stationary phase powder, and dried

Sources & evidence

ORD record
ord-43422afbae114099b22d27b3ef833b18
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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