Methyl iodide → HCID 59178184, compound

HRID 1643417Notes

Reaction equation

HRID 1643417 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[CH3:12]I>CN(C=O)C.[Ag]=O>[OH:1][C@H:2]1[C@@H:6]([O:7][CH3:12])[CH2:5][C@@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 45089886HCID 45089886, compound

Product 1

HCID 59178184HCID 59178184, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl (3S,4R)-3,4-dihydroxycyclopentanecarboxylate (0.481 g, 3 mmol), freshly prepared silver oxide (0.348 g, 1.500 mmol) and methyl iodide (0.375 ml, 6.00 mmol) were combined in DMF and allowed to stir for 3 hrs. The reaction mixture was filtered through celite and washed with 15 ml of ether. The organic filtrate was washed 2× with brine, dried over sodium sulfate and evaporated. Purification by silica gel chromatography eluting with 20-40% acetone hexane gave the title compound. 1H NMR (500 MHz, CDCl3) δ 2.01-2.18 (m, 4H), δ 2.48 (s, br, 1H), δ 2.77 (m, 1H), δ 3.40 (s, 3H) δ 3.6-3.65 (m, 1H), δ 3.71 (s, 3H), δ 4.10 (m, 1H)

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with 15 ml of ether
  3. washThe organic filtrate was washed 2× with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customPurification by silica gel chromatography
  7. washeluting with 20-40% acetone hexane

Sources & evidence

ORD record
ord-901392650f084ed9b5016b878e250c42
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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