Methyl iodide → HCID 70239688, compound

HRID 443238Notes

Reaction equation

HRID 443238 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C@H:10]([OH:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:24]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[C@H:10]([O:21][CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70204515HCID 70204515, compound

Product 1

HCID 70239688HCID 70239688, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-N-t-butoxycarbonyl-4-(3-methylphenyl)-3 hydroxy piperidine (117 mg, 0.402 mmol), in DMF (2 ml) at 0° C. was added sodium hydride (24 mg of a 60% dispersion in mineral oil, 0.803 mmol). After 10 min, methyl iodide (0.050 ml, 0.803 mmol) was added and the reaction allowed to warm to room temperature over 16 hrs. The reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc. The organic extracts were washed with brine and dried, (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, 10-15% EtOAc in hexanes) afforded the title compound as an oil.

Workup

  1. customThe reaction was quenched by the addition of saturated NH4Cl solution (5 ml) and extraction with EtOAc
  2. washThe organic extracts were washed with brine
  3. customdried
  4. custom(MgSO4) and the solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e207456e674243f392e5d26d9f2ef570
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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