Dimethyl Sulfoxide → Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate

HRID 2368101Notes

Reaction equation

HRID 2368101 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.C(N(CC)CC)C.CS(C)=O>O>[O:1]=[CH:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 57517495Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

Product 1

HCID 57517496Benzyl 4-(2-oxoethoxy)piperidine-1-carboxylateYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate (6.33 g), triethylamine (15.9 mL) and dimethyl sulfoxide (30 mL) were added dropwise a mixture of sulfur trioxide pyridine complex (10.8 g) and dimethyl sulfoxide (30 mL) at room temperature, and the obtained mixture was stirred at room temperature for 1 hr. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with 1M hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.28 g).

Workup

  1. additionwere added dropwise
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1M hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-80f163d2f83b40fda80472bb07487570
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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