Dimethylformamide → Diisopropylether hexane

HRID 1796803Notes

Reaction equation

HRID 1796803 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5](S(N2[CH2:16][C@H:15]3[CH2:17]C(C)(C)[C@@H:12]2[C:13](=O)[O:14]3)(=O)=O)=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH:15]([O:14][CH:13]([CH3:12])[CH3:22])([CH3:16])[CH3:17].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 69597672HCID 69597672, compound2×

Product 1

HCID 21881879Diisopropylether hexane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (1R,4R)-5-(4-hydroxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVIII, 0.15 g, 0.48 mmol), the appropriate alkyl halide (0.97 mmol), potassium carbonate (0.13 g, 0.97 mmol) and dimethylformamide (1 ml) was shaken at about 50° C. for about 24 hours. The mixture was diluted with ethyl acetate, washed 4 times with water, dried over sodium sulfate, filtered and concentrated. Trituration of the residue from isopropyl ether-hexane afforded the corresponding (1R,4R)-5-(4-arylmethoxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXIX) as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-23900550ca0643b392689f5ce8b4ac86
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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