Water → 1-Benzhydryl-3-cyclopropyl-3-methoxyazetidine

HRID 1187750Notes

Reaction equation

HRID 1187750 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH:19]2[CH2:21][CH2:20]2)([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.[H-].[Na+].[CH3:24]I.O>CN(C)C=O>[CH:1]([N:14]1[CH2:17][C:16]([CH:19]2[CH2:20][CH2:21]2)([O:18][CH3:24])[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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 532567381-Benzhydryl-3-cyclopropylazetidin-3-ol

Product 1

HCID 670081921-Benzhydryl-3-cyclopropyl-3-methoxyazetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

334 mg of 1-benzhydryl-3-cyclopropylazetidin-3-ol was dissolved in dimethylformamide, and 72 mg of 60% sodium hydride was added thereto, and the mixture was stirred at room temperature for 30 minutes. 112 μl of methyl iodide was added thereto, and the mixture was further stirred at room temperature for 2 hours. To the reaction solution was added water and the mixture was subjected to extraction with diethyl ether, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 280 mg of the objective compound.

Workup

  1. stirringthe mixture was further stirred at room temperature for 2 hours
  2. extractionthe mixture was subjected to extraction with diethyl ether
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae490cf6bace43a49f8f773f2e4f5483
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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