Water → HCID 58495740, compound

HRID 2359351Notes

Reaction equation

HRID 2359351 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[CH3:20][N:21]([CH3:27])[S:22]([CH:25]=[CH2:26])(=[O:24])=[O:23].O>O1CCCC1>[CH3:20][N:21]([CH3:27])[S:22]([CH2:25][CH2:26][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylateHCID 19037148N,N-dimethylethene-1-sulfonamide

Product 1

HCID 58495740HCID 58495740, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzyl 4-hydroxypiperidine-1-carboxylate (5.0 g, 21.2 mmol) was dissolved in tetrahydrofuran (100 ml), and while cooling with ice, sodium hydride (content 55%) (1.0 g, 22.9 mmol) was added. The resulting mixture was stirred for 30 minutes while cooling with ice, to which 20 mL of a solution of N,N-dimethylethenesulfonamide in tetrahydrofuran (3.0 g, 22.2 mmol) was added dropwise over five minutes. The resulting mixture was stirred for 30 minutes while cooling with ice, and then for three hours at room temperature. The resulting reaction liquid was poured into water and then extracted with ethyl acetate. The resulting organic layer was sequentially washed with water and saturated brine, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V) to give the desired title compound (4.9 g, yield 62%).

Workup

  1. additionwas added
  2. additionwas added dropwise over five minutes
  3. stirringThe resulting mixture was stirred for 30 minutes
  4. temperaturewhile cooling with ice
  5. waitfor three hours at room temperature
  6. customThe resulting reaction liquid
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic layer was sequentially washed with water and saturated brine
  9. dry with materialdried over sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V)

Sources & evidence

ORD record
ord-ed02c9354c1e4f308026464e854c17c7
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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