Cesium carbonate → HCID 68160022, compound

HRID 1468762Notes

Reaction equation

HRID 1468762 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH2:11][CH2:10][C@H:9]([CH2:12][OH:13])[CH2:8]1.I[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1.CC(C)C(C1CCCCC1=O)=O>C(OCC)(=O)C.[Cu]I.CN(C)C=O>[S:17]1[CH:18]=[CH:19][C:15]([N:7]2[CH2:11][CH2:10][C@H:9]([CH2:12][OH:13])[CH2:8]2)=[CH:16]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 663323-IodothiopheneHCID 7446911(3S)-3-PyrrolidinemethanolHCID 114693012-(2-Methylpropanoyl)cyclohexan-1-one

Product 1

HCID 68160022HCID 68160022, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A dried round bottom flask was charged with copper(I) iodide (0.10 g, 0.53 mmol), cesium carbonate (3.58 g, 11 mmol). The flask was evacuated and backfilled with nitrogen. Under the flow of nitrogen, (S)-pyrrolidin-3-yl-methanol (0.80 g, 7.9 mmol), 3-iodothiophene (0.54 ml, 5.3 mmol), 2-(2-methyl-1-oxopropyl)cyclohexanone (0.35 ml, 2.1 mmol), and N,N-dimethylformamide (5 ml) were added. The mixture was allowed to stir under nitrogen at ambient temperature for 12 hours. The mixture was diluted with ethyl acetate, passed through a glass filter to remove the inorganic salts and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=9/1 to 1/1) to afford (S)-[1-(thiophen-3-yl)pyrrolidin-3-yl]methanol (0.41 g, 2.2 mmol, 42%) as a brown oil. In the manner as above (2)-(6), with the use of methyl (3R)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate instead of methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate, (R)-[1-(thiophen-3-yl)pyrrolidin-3-yl]methanol was obtained (0.19 g, 1.0 mmol).

Workup

  1. customThe flask was evacuated
  2. filtrationfilter
  3. customto remove the inorganic salts
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=9/1 to 1/1)

Sources & evidence

ORD record
ord-a5f478988fdb40afbd7d16aebb9a62a7
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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