Methyl iodide → Tert-butyl 4-methoxypiperidine-1-carboxylate

HRID 586711Notes

Reaction equation

HRID 586711 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.I[CH3:18]>O1CCCC1.O>[CH3:18][O:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21955381Tert-butyl 4-methoxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.19 g, 60% in mineral oil, 29.7 mmol) was added portionwise to a cooled (10° C.) solution of tert-butyl 4-hydroxy-1-piperidinecarboxylate (Bioorg. Med. Chem. Lett. 10; 24; 2000; 2815) in tetrahydrofuran (80 mL), and the suspension stirred at room temperature for 1 hour. Iodomethane (1.85 mL, 29.7 mmol) was added, and the reaction stirred at 50° C. for 20 hours. The mixture was diluted with water (50 mL), extracted with ethyl acetate (2×150 mL) and the combined organic extracts washed with saturated sodium bicarbonate solution (50 mL), dried (MgSO4) and evaporated under reduced pressure, to afford the title compound as a golden oil, 5.24 g.

Workup

  1. stirringthe reaction stirred at 50° C. for 20 hours
  2. extractionextracted with ethyl acetate (2×150 mL)
  3. washthe combined organic extracts washed with saturated sodium bicarbonate solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-668c704eb7004847ada7a0f2ee8485ef
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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