Methyl iodide → Benzyl 4-methoxypiperidine-1-carboxylate

HRID 915914Notes

Reaction equation

HRID 915914 reaction equation
O1CCC[CH2:2]1.[OH:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1.[H-].[Na+].CI>C(OCC)(=O)C>[CH3:2][O:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 23024301Benzyl 4-methoxypiperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 20 ml tetrahydrofuran solution of 1.87 g (7.95 mmol) of benzyl 4-hydroxy-1-piperidinecarboxylate, 413 mg (60% in oil, 10.33 mmol) of sodium hydride and 792 μl (12.72 mmol) of methyl iodide were added at 0° C., and the mixture was stirred at room temperature for 16.5 hours. Then, the reaction mixture was diluted with ethyl acetate, and washed with water. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 2.08 g (94%) of the captioned compound.

Workup

  1. washwashed with water
  2. dry with materialThe washed system was dried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-3faf55943fe7472bbbcdb55c630b4593
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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