Dimethylformamide → Diisopropylether hexane

HRID 1796798Notes

Reaction equation

HRID 1796798 reaction equation
[C:1]([O:5][C:6]([CH:8]1[C:13](O)(C)[CH2:12][CH2:11][CH2:10]N1S(C1C=CC(O)=CC=1)(=O)=O)=O)([CH3:4])([CH3:3])C.[C:26](=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C>[CH:6]([O:5][CH:1]([CH3:3])[CH3:4])([CH3:8])[CH3:26].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:8][CH3:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 69597615HCID 69597615, compound

Product 1

HCID 21881879Diisopropylether hexane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-hydroxy-1-(4-hydroxy-benzenesulfonyl)-3-methyl-piperidine-2-carboxylic acid tert-butyl ester (XIX, 0.20 g, 0.54 mmol), the appropriate alkyl halide (0.81 mmol), cesium carbonate (0.35 g, 1.1 mmol) and dimethylformamide (1 ml) was stirred at about 23° C. for about 24 hours. The mixture was diluted with ethyl acetate, washed 5 times with water, dried over sodium sulfate, filtered and concentrated. Trituration of the residue from isopropyl ether-hexane afforded the corresponding 3-hydroxy-1-(4-arylmethoxy-benzenesulfonyl)-3-methyl-piperidine-2-carboxylic acid tert-butyl ester (compound of formula XX) as a colorless solid.

Workup

  1. washwashed 5 times with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-852e16a3086b40619bed72d7999bf697
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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