Methyl iodide → tert-Butyl 4-formyl-4-methylpiperidine-1-carboxylate

HRID 1809609Notes

Reaction equation

HRID 1809609 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:2].[CH3:16]C(C)([O-])C.[K+].IC>ClCCl.[Cl-].[Na+].O>[CH:1]([C:3]1([CH3:16])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22248051tert-Butyl 4-formyl-4-methylpiperidine-1-carboxylateYield 43.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl 4-formylpiperidine-1-carboxylate (35.0 g, 164.1 mmol) was dissolved in dichloromethane (200 mL) and cooled to 0° C. Potassium tert-butoxide (23.9 g, 213 mmol) was added followed by addition of iodomethane (69.9 g, 492 mmol). The reaction was stirred at 0° C. for 30 minutes, and then warmed to ambient temperature and stirred for 1.5 hr. The reaction mixture was poured into brine (400 mL) and the organic layer was separated, dried, and filtered, and concentrated and purified by silica gel to provide tert-butyl 4-formyl-4-methylpiperidine-1-carboxylate (16.36 g, 72.0 mmol, 43.8% yield).

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for 1.5 hr
  3. customthe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel

Sources & evidence

ORD record
ord-8c5035db54fb4d349527efacb3730b76
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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