Pyridine → Methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate

HRID 605513Notes

Reaction equation

HRID 605513 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:12][CH2:11][C:8]([C:13]([O:15][CH3:16])=[O:14])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2.N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.C(OCC)(=O)C>[CH3:23][S:24]([O:1][CH2:2][CH2:3][CH2:4][C:5]12[CH2:10][CH2:9][C:8]([C:13]([O:15][CH3:16])=[O:14])([CH2:11][CH2:12]1)[CH2:7][CH2:6]2)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22591716Methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 22591707Methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydroxyester 2-4 (430 mg, 1.9 mmol) was dissolved in 2.5 mL of anhydrous methylene chloride under nitrogen atmosphere, treated with pyridine (0.5 mL) and methanesulfonyl chloride (0.368 mL, 4.8 mmol) and stirred for 4 h at room temperature. The mixture was diluted with 100 mL of ethyl acetate and washed with 1N aqueous HCl, saturated aqueous sodium bicarbonate, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated. The crude methyl 4-{3-[(methylsulfonyl)oxy]propyl}bicyclo-[2.2.2]octane-1-carboxylate (2-5) thus afforded was used without purification in the next reaction. 1H NMR (500 MHz, CDCl3): δ 4.22 (2H, t, J=7.5 Hz), 3.68 (3H, s), 3.04 (3H, s), 1.82 (6H, m), 1.70 (2H, m), 1.44 (6H, m), 1.24 (2H, m) ppm.

Workup

  1. washwashed with 1N aqueous HCl, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-c92b50433d5f48bc886c19d346be3f29
Source dataset
uspto-grants-2011_03
Patent number
US07915252B2

Reaction notes

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