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

HRID 1869463Notes

Reaction equation

HRID 1869463 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[CH3:17][Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]#[N:15])([CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 46835621tert-Butyl 4-cyano-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-cyano-piperidine-1-carboxylic acid tert-butyl ester (4.52 g, 20 mmol) in THF (50 mL) was added LHMDS in THF (24 mL, 24 mmol) at 0° C. After stirring at 0° C. for 1 hour, MeI (5.7 g) was added. The reaction mixture was kept at 0° C. for 2 hours, then partitioned between EtOAc and H2O. After concentration in vacuo, the residue was purified by silica column chromatography with EtOAc/hexanes to give the desired product.

Workup

  1. waitThe reaction mixture was kept at 0° C. for 2 hours
  2. custompartitioned between EtOAc and H2O
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by silica column chromatography with EtOAc/hexanes

Sources & evidence

ORD record
ord-9281bceadf32437483d70449f4b507d9
Source dataset
uspto-grants-2009_12
Patent number
US07638541B2

Reaction notes

Loading…