Triethylamine → 3-[(Methylsulfonyl)oxy]-2-piperidinone

HRID 1752238Notes

Reaction equation

HRID 1752238 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[O:8]=[C:3]1[CH:2]([O:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:7][CH2:6][CH2:5][NH:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2649903-Hydroxypiperidin-2-one

Product 1

HCID 144568963-[(Methylsulfonyl)oxy]-2-piperidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-hydroxy-piperidin-2-one (500 mg, 4.34 mmol, 1.0 eq) and triethylamine (0.908 mL, 6.51 mmol, 1.5 eq) in dichloromethane (3 mL) at 0° C. was added dropwise methanesulfonyl chloride (497 mg, 4.34 mmol, 1.0 eq) dissolved in dichloromethane (1 mL). The reaction was complete within 30 min as judged by LCMS. An orange precipitate was filtered, redissolved in dichloromethane and purified by column chromatography (MeOH/CH2Cl2) to give the title compound as a white waxy solid (204 mg, 1.056 mmol, 24.3% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 5.78 (br. s, 1H) 4.94-5.05 (m, 1H) 3.30-3.44 (m, 2H) 3.27 (s, 3H) 2.24-2.37 (m, 1H) 2.08-2.21 (m, 1H) 1.98-2.08 (m, 1H) 1.79-1.96 (m, 1H). MS (m/z, MH+): 193.7

Workup

  1. filtrationAn orange precipitate was filtered
  2. dissolutionredissolved in dichloromethane
  3. custompurified by column chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e7799abcec934755befe323f78fae586
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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