Dichloromethane → t-Butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate

HRID 1172260Notes

Reaction equation

HRID 1172260 reaction equation
ClCCl.[OH:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O>[CH3:32][S:33]([O:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=1)(=[O:35])=[O:34]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58105232t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate

Product 1

HCID 58105230t-Butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 200 mL round-bottom flask, 50 mL of dichloromethane, 2.78 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate and 2.0 g of diisopropylethylamine were added, and the mixture was stirred at ice temperature for 10 minutes. To the reaction mixture, 0.89 mL of methanesulfonyl chloride was added dropwise, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=3:1) to give 2.28 g of t-butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b9ccf3b43170427fac9e935c89d62643
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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