Water → HCID 67238312, compound

HRID 1712109Notes

Reaction equation

HRID 1712109 reaction equation
C1([SiH3])C=CC=CC=1.O.[N+:9](/[CH:12]=[C:13](/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)\[CH3:14])([O-:11])=[O:10]>CC(C)([O-])C.[Cu+].C1(C)C=CC=CC=1.C[C@H](P(C1CCCCC1)C1CCCCC1)[C]1[C](P(C2C=CC=CC=2)C2C=CC=CC=2)[CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe]>[N+:9]([CH2:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH3:14])([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 962Water2×HCID 12752PhenylsilaneHCID 67238404HCID 67238404, compound

Product 1

HCID 67238312HCID 67238312, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178461696HCID 178461696, compoundCatalystHCID 1140TolueneSolvent2×HCID 11252043AGN-PC-005B6WSolvent

Procedure

In a 10 mL Schlenk-flask, 6.8 mg of copper (I) tert-butoxide and 55 μmol of (S)—(R)-JOSIPHOS were dissolved in 5 ml of toluene. After stirring for 30 minutes at room temperature to give an asymmetric copper complex. This solution to the amount containing 10 μmol of the asymmetric copper complex were mixed with 4.9 ml of toluene, and 6 μL (0.1 mmol) of poly(methylhydrosiloxane) (15-40 mPas (20° C.), d=1.004 g/mL, nD20=1.398, produced by Fluka) were added thereto. Further, 185 μL of (1.5 mmol) of phenylsilane and 27 μL (1.5 mmol) of water were added. After stirring for 5 minutes, 1 mmol of (E)-1-nitro-2-(pyridin-2-yl)-1-propene was added, and the mixture was further stirred for 24 hours at room temperature. Water was added to the reaction mixture and the product was extracted with diethyl ether (30 mL×2). After drying over sodium sulfate, the solvent was evaporated. The residue was purified by flash chromatography (silica gel, hexane/ethyl acetate) to provide optically active 1-nitro-2-(pyridin-2-yl)propane.

Workup

  1. customto give an asymmetric copper complex
  2. additionThis solution to the amount containing 10 μmol of the asymmetric copper complex
  3. customnD20=1.398, produced by Fluka)
  4. additionwere added
  5. stirringAfter stirring for 5 minutes
  6. stirringthe mixture was further stirred for 24 hours at room temperature
  7. extractionthe product was extracted with diethyl ether (30 mL×2)
  8. dry with materialAfter drying over sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by flash chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-00e16418f2d7483489aa6c31a6f93a01
Source dataset
uspto-grants-2010_09
Patent number
US07790900B2

Reaction notes

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