Water → 1-Benzhydryl-3-methoxyazetidine

HRID 2217221Notes

Reaction equation

HRID 2217221 reaction equation
Cl.[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:9]2[CH2:12][CH:11]([OH:13])[CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22]COC(C)=O.O>CN(C=O)C>[C:14]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]2[CH2:12][CH:11]([O:13][CH3:22])[CH2:10]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 28017261-benzhydrylazetidin-3-ol Hydrochloride

Product 1

HCID 5975241-Benzhydryl-3-methoxyazetidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(diphenylmethyl)-3-azetidinol hydrochloride (5.0 g) in DMF (25 ml), was added sodium hydride under ice-bath cooling. After 10 minute stirring at the same temperature, the mixture was allowed to warm to 25° C. and then stirred for 15 hours. EtOAc (500 ml) and water (200 ml) were poured into the mixture. The organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel; 200 ml, toluene:EtOAc=15:1-8:1) to give 1-(diphenylmethyl)-3-methoxyazetidine (3.41 g).

Workup

  1. temperaturecooling
  2. stirringstirred for 15 hours
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel; 200 ml, toluene:EtOAc=15:1-8:1)

Sources & evidence

ORD record
ord-98d0e8ffe7cd4033b3598b66d382ccdd
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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