Methyl iodide → 1-(Diphenylmethyl)-3-ethyl-3-methoxyazetidine

HRID 1091293Notes

Reaction equation

HRID 1091293 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH2:19][CH3:20])([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.[CH3:21]I.[H-].[Na+]>CN(C=O)C>[CH:1]([N:14]1[CH2:17][C:16]([CH2:19][CH3:20])([O:18][CH3:21])[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 19423788HCID 19423788, compound

Product 1

HCID 665918001-(Diphenylmethyl)-3-ethyl-3-methoxyazetidineYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (50 mL) solution of 1-benzhydryl-3-ethylazetidin-3-ol (2.18 g, 8.15 mmol), methyl iodide (0.51 mL, 8.15 mmol) and 60% sodium hydride (0.65 g, 16.31 mmol) were added at 0° C. under a nitrogen stream, and the mixture was stirred for 1.5 hours at the same temperature. This 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 separated by filtration, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 25S, ethyl acetate/n-hexane=1/9-4/6), to obtain the title compound (1.18 g, 52%) as an oily matter.

Workup

  1. additionThis 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 separated by filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 25S, ethyl acetate/n-hexane=1/9-4/6)

Sources & evidence

ORD record
ord-3840c29edc9640e184095a49c7d24bf4
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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