Methyl iodide → HCID 68432352, compound

HRID 1867366Notes

Reaction equation

HRID 1867366 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:15][OH:16])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH3:18].[H-].[Na+].OS([O-])(=O)=O.[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:15][O:16][CH3:18])([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 22258928Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylate2×

Product 1

HCID 68432352HCID 68432352, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.37 g (1.60 mmol) of (rac)-3-hydroxymethyl-3-methyl-piperidine-1-carboxylic acid tert-butyl ester (intermediate 30B) and 0.20 ml (3.20 mmol) of iodomethane in 15 ml of DMF was treated at 0° C. with 0.08 g (1.92 mmol) of NaH (55% in oil). The reaction was stirred for 2 h at 0° C., neutralized with cold aqueous 10% KHSO4 and extracted with Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane/EtOAc 95:5) to yield 0.25 g (64%) of the title compound as colorless liquid. MS: 244.1 (MH+).

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by flash silica gel column (n-heptane/EtOAc 95:5)

Sources & evidence

ORD record
ord-4eabf206894a443792c417e0d64a2f74
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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