Phosphorus tribromide → 1-Allyloxycarbonyl-2-methoxycarbonyl-4-trimethylsilylethynyl-3-pyrroline

HRID 1029623Notes

Reaction equation

HRID 1029623 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](O)([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH:8]1[C:19]([O:21][CH3:22])=[O:20])=[O:6])[CH:2]=[CH2:3].P(Br)(Br)Br.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:8]1[C:19]([O:21][CH3:22])=[O:20])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 151172301-Allyloxycarbonyl-4-hydroxy-2-methoxycarbonyl-4-trimethylsilylethynylpyrrolidineHCID 22728543Water ethylacetate

Product 1

HCID 151172311-Allyloxycarbonyl-2-methoxycarbonyl-4-trimethylsilylethynyl-3-pyrrolineYield 45.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-allyloxycarbonyl-4-hydroxy-2-methoxycarbonyl-4-trimethylsilylethynylpyrrolidine (7.0 g) in toluene (70 ml) was slowly added phosphorus tribromide (2.25 ml) at room temperature and the mixture was stirred at room temperature for one day. The reaction mixture was then poured into iced water-ethyl acetate. The aqueous layer was then separated and extracted with ethyl acetate twice. The organic layers were combined, washed with saturated aqueous sodium hydrogen carbonate solution twice and further with water and aqueous sodium chloride solution successively, and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to give 1-allyloxycarbonyl-2-methoxycarbonyl-4-trimethylsilylethynyl-3-pyrroline (3.0 g).

Workup

  1. customat room temperature
  2. customThe aqueous layer was then separated
  3. extractionextracted with ethyl acetate twice
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution twice
  5. dry with materialfurther with water and aqueous sodium chloride solution successively, and dried over anhydrous magnesium sulfate
  6. distillationFinally the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-35c7f56c1a244c33b2382e6f8b8341ac
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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