Methyl iodide → 1-Benzhydryl-3-methoxy-3-methylazetidine

HRID 1091291Notes

Reaction equation

HRID 1091291 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH3:19])([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20]I.[H-].[Na+]>CN(C=O)C>[CH:1]([N:14]1[CH2:17][C:16]([O:18][CH3:20])([CH3:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 102439891-Benzhydryl-3-methylazetidin-3-ol

Product 1

HCID 152086291-Benzhydryl-3-methoxy-3-methylazetidineYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (2 mL) solution of 1-benzhydryl-3-methylazetidin-3-ol (123 mg, 0.486 mmol), methyl iodide (33.2 μl, 0.534 mmol) and 60% sodium hydride (29 mg, 0.729 mmol) were added at 0° C. under a nitrogen stream, and the mixture was stirred for one hour at the same temperature. The reaction liquor was poured onto ice water, and the mixture was extracted with ethyl acetate. The extract was washed with ice water and saturated brine in this order, and then dried over anhydrous sodium sulfate. Sodium sulfate was removed, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by thin layer chromatography (ethyl acetate/n-hexane=10/1, v/v), to obtain the title compound (38 mg, 29%) as an oily matter.

Workup

  1. additionThe reaction liquor was poured onto ice water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with ice water and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSodium sulfate was removed
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe obtained residue was purified by thin layer chromatography (ethyl acetate/n-hexane=10/1

Sources & evidence

ORD record
ord-220b24ed968c41a7bde93056dc0a1121
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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