HCID 13969923, compound → HCID 22664969, compound

HRID 392601Notes

Reaction equation

HRID 392601 reaction equation
[C:1]([C:9]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.O>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 13969923HCID 13969923, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22664969HCID 22664969, compoundYield 694.6%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

(S)-tBuBisP*-RuBr2 (25 mg) was placed in a reaction vessel and deaerated. After substitution with argon, a mixture of ethyl 1-benzoylcyclopropanecarboxylate (3.3 g, 1.0 mmol) and methanol-water (10/1) (33 ml) was added. The mixture was stirred at 70° C. and hydrogen pressure (6 kg/cm2) for 24 h, after which the reaction mixture was concentrated. This was concentrated to dryness, diluted with ethyl acetate, washed with water and purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (1.53 g, 46.3%) as a colorless oil. The enantiomer excess of this product was measured by high performance liquid chromatography (Condition F) and found to be 85%.

Workup

  1. additionwas added
  2. concentrationafter which the reaction mixture was concentrated
  3. concentrationThis was concentrated to dryness
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-271070d01420498789cbf5a69baeb4a1
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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