Sodium Carbonate → 1-Benzhydryl-3-cyclopropylazetidin-3-ol

HRID 2043478Notes

Reaction equation

HRID 2043478 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=[O: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.[CH:19]1([Mg]Br)[CH2:21][CH2:20]1.O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178420628HCID 178420628, compound

Product 1

HCID 532567381-Benzhydryl-3-cyclopropylazetidin-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 mg of 1-benzhydrylazetidin-3-one dissolved in 3.8 ml of tetrahydrofuran was added to 2 ml of 1M cyclopropyl magnesium bromide/tetrahydrofuran solution under ice water cooling, and the mixture was allowed to warm to room temperature and stirred for 30 minutes. The reaction solution was poured into a saturated aqueous solution of sodium carbonate 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 334 mg of the objective compound.

Workup

  1. extractionthe mixture was subjected to extraction with diethyl ether
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cfc7362f15cf4197bd85ec23a7c53926
Source dataset
uspto-grants-2013_11
Patent number
US08586591B2

Reaction notes

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