Methyl iodide → benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate

HRID 81139Notes

Reaction equation

HRID 81139 reaction equation
[F:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([OH:8])[CH2:5][N:4]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH3:19]I.[H-].[Na+]>C1COCC1>[F:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([O:8][CH3:19])[CH2:5][N:4]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57364082HCID 57364082, compound

Product 1

HCID 86724496benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2S,4R)-2-(fluoromethyl)-4-hydroxypyrrolidine-1-carboxylate (500 mg, 1.97 mmol) in THF (6.6 mL) at 0° C. was added methyl iodide (0.43 mL, 3.44 mmol) followed by sodium hydride (104 mg, 4.34 mmol). The mixture was stirred for 2 hours at room temperature. The reaction was quenched with ice, and diluted with diethyl ether. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate. MS ESI calc'd. for C14H18FNO3 [M+H]+ 268. found 268.

Workup

  1. customThe reaction was quenched with ice
  2. additiondiluted with diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e63ec6a922ea44958d4e06221a54b723
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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