Sodium Bicarbonate → HCID 19423788, compound

HRID 1091292Notes

Reaction equation

HRID 1091292 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.[CH2:19]([Mg]Br)[CH3:20].C(=O)([O-])O.[Na+]>O1CCCC1>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 19423788HCID 19423788, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a tetrahydrofuran solution (10 mL) of 1-benzhydrylazetidin-3-one (3.23 g, 13.61 mmol), a 1M-tetrahydrofuran solution of ethylmagnesium bromide (13.61 mL, 27.22 mmol) was added at −78° C. under a nitrogen stream, and the mixture was allowed to warm to −10° C. over 5 hours. 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: 40M, ethyl acetate/n-hexane=1/9 to 6/4), to obtain the title compound (2.18 g, 60%) as an oily matter.

Workup

  1. filtrationThen, the reaction liquor was filtered through celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  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: 40M, ethyl acetate/n-hexane=1/9 to 6/4)

Sources & evidence

ORD record
ord-644f17aedce74d7fad738d794b62b014
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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