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

HRID 1063902Notes

Reaction equation

HRID 1063902 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:17]I>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

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 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 60% sodium hydride (939 mg) in dimethylformamide (30 ml) was added 1-t-butoxycarbonyl-4-hydroxypiperidine (3.15 g) under ice-water cooling and the mixture was stirred at 0° C. for 0.5 hour. To the solution was added methyl iodide (1.17 ml) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (3:1) to give 1-t-butoxycarbonyl-4-methoxypiperidine as colorless oil (2.84 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. customThe mixture was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a mixture of hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-3a4fabd7e7fe46fd98fe8c2a9a349a71
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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