Water → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one

HRID 2255661Notes

Reaction equation

HRID 2255661 reaction equation
[Si:1]([O:8][C@H:9]([CH3:27])[C@H:10]([CH2:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:11](OCC)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=C(C)C=C(C)C=1[Mg]Br.O>O1CCCC1>[Si:1]([O:8][C@@H:9]([C@@H:10]1[CH2:16][N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:11]1=[O:12])[CH3:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 57031907ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoateHCID 178425415HCID 178425415, compound

Product 1

HCID 54758409(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-oneYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoate (6 g) in tetrahydrofuran (303 ml) was added dropwise a solution of mesitylmagnesium bromide (1M, 24.3 ml) in tetrahydrofuran at room temperature. After stirring for 30 minutes, water (10 ml) was added dropwise to the reaction mixture and the solvent was removed under reduced pressure. To the residue were added ethyl acetate and water, then the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and an aqueous sodium chloride in turn and then dried over magnesium sulfate. The resultant solution was evaporated under reduced pressure and the residue was column-chromatographed on silica gel (eluent : a mixture of hexane and ethyl acetate, 3:1) to give (3S*)-3-[(1R*)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one (4.8 g), which contained about 2% of the corresponding (3R*), (1R*)-isomer.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionTo the residue were added ethyl acetate and water
  3. customthe aqueous layer was separated
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic layers were washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water
  6. dry with materialan aqueous sodium chloride in turn and then dried over magnesium sulfate
  7. customThe resultant solution was evaporated under reduced pressure
  8. customthe residue was column-chromatographed on silica gel (eluent
  9. additiona mixture of hexane and ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-a049cb945b734cda8a807be1937953e9
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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