Sodium Bicarbonate → 1-Benzhydryl-3-methylazetidin-3-ol

HRID 1091290Notes

Reaction equation

HRID 1091290 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.[CH3:19][Mg]I.C(=O)([O-])O.[Na+]>O1CCCC1>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418373HCID 178418373, compound

Product 1

HCID 102439891-Benzhydryl-3-methylazetidin-3-olYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (10 mL) of 1-benzhydrylazetidin-3-one (530 mg, 1.94 mmol), methylmagnesium iodide (0.84 M ether solution) (4.62 mL, 3.88 mmol) was added at 0° C. under a nitrogen stream, and the mixture was stirred for one hour at the same temperature. A saturated aqueous solution of sodium hydrogen carbonate (20 mL) was added to the reaction liquor, and the mixture was stirred for 15 minutes. Then, the reaction liquor was filtered through celite, and the filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, and then dried over anhydrous sodium sulfate. Sodium sulfate was separated by filtration, and the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, ethyl acetate/n-hexane=1/4 to ethyl acetate), to obtain the title compound (511 mg, quant.) as an oily matter.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. filtrationThen, the reaction liquor was filtered through celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customSodium sulfate was separated by filtration
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, ethyl acetate/n-hexane=1/4 to ethyl acetate)

Sources & evidence

ORD record
ord-cab0e86c91904b1db4832b685d569637
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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