Allyl bromide → HCID 14989077, compound

HRID 2380125Notes

Reaction equation

HRID 2380125 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(NC(C)C)(C)C.[CH:13]([C@H:16]1[CH2:20][O:19][C:18](=[O:21])[N:17]1[C:22](=[O:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:15])[CH3:14].C(Br)C=C.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:24]([C@H:23]([CH2:3][CH:2]=[CH2:1])[C:22]([N:17]1[C@@H:16]([CH:13]([CH3:15])[CH3:14])[CH2:20][O:19][C:18]1=[O:21])=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 5

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 10467835(S)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 14989077HCID 14989077, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

8.61 ml (13.8 mmoles) of butyllithium (as a 1.6M hexane solution) were added dropwise, at -78° C. and under an atmosphere of nitrogen, to a solution of 1.93 ml (13.8 mmoles) of diisopropylamine in 20 ml of anhydrous tetrahydrofuran. The mixture was stirred for 30 minutes, and then a solution of 3.00 mg (11.5 mmoles) of 4(S)-isopropyl-3-(3-phenylpropionyl)-2-oxazolidinone (prepared as described in Preparation 16) in 10 ml of anhydrous tetrahydrofuran was added dropwise thereto, and the mixture was stirred for 1 hour. At the end of this time, 2.99 ml (34.6 mmoles) of allyl bromide were added to the mixture, and the mixture was stirred for 12 hours, whilst allowing it to return gradually to room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 5:1 by volume mixture of hexane and ethyl acetate as eluent), to give 2.14 g (yield 62%) of the title compound as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe mixture was stirred for 12 hours
  3. customto return gradually to room temperature
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by medium pressure silica gel column chromatography (
  8. additionby volume mixture of hexane and ethyl acetate as eluent),

Sources & evidence

ORD record
ord-da75244596c34f5ba0d0c9711968cea0
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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