Methyl iodide → benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylate

HRID 81147Notes

Reaction equation

HRID 81147 reaction equation
[OH:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:5]([CH3:18])[CH2:4][CH2:3]1.[CH3:19]I.[H-].[Na+]>C1COCC1>[CH3:19][O:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:5]([CH3:18])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86724500benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate

Product 1

HCID 86724501benzyl (2R)-5-methoxy-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of benzyl (2R)-5-hydroxy-2-methylpiperidine-1-carboxylate (368 mg, 1.47 mmol) dissolved in THF (4.9 mL) at 0° C. was added methyl iodide (0.32 mL, 5.08 mmol) followed by sodium hydride (78 mg, 3.25 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 (2R)-5-methoxy-2-methylpiperidine-1-carboxylate. MS ESI calc'd. for C15H21NO3 [M+H]+ 264. found 264.

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-374abcd4435e45fb8e8e928c9c3a2988
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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