Methyl iodide → HCID 60128538, compound

HRID 2308108Notes

Reaction equation

HRID 2308108 reaction equation
[OH:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[H-].[Na+].[CH3:20]I>C1COCC1>[OH:1][C@H:2]1[C@H:6]([O:7][CH3:20])[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10331712HCID 10331712, compound

Product 1

HCID 60128538HCID 60128538, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (3R,4R)-3,4-dihydroxypyrrolidine-1-carboxylate (3.81 g, 16.1 mmol) in 60 mL THF was added NaH (0.803 g, 20.07 mmol). The reaction mixture was stirred at room temperature for 15 min, CH3I (2.0 mL, 32.2 mmol) was added and stirred at room temperature overnight. The reaction mixture was quenched with H2O (80 mL) and extracted with EtOAc (2×100 mL). The organic layer was dried and concentrated. The residue was purified by flash column chromatography (1˜2% CH3OH in CH2Cl2) to give a white solid (1.12 g, 28%). 1H NMR (CDCl3) δ 7.36-7.29 (5H, m), 5.12 (2H, s), 4.28-4.27 (1H, m), 3.72-3.37 (5H, m), 3.35 (3H, s), 1.95-1.89 (1H, m). ESIMS (MH+): 252.05.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was quenched with H2O (80 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (1˜2% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-a930792e358f4e39a19cd5e2b30c435a
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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