HCID 22664973, compound → HCID 22664963, compound

HRID 392600Notes

Reaction equation

HRID 392600 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[C:4]([C:6]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[H][H]>CO.O>[Cl:1][C:2]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:3]=1[CH:4]([OH:5])[C:6]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 22664973HCID 22664973, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22664963HCID 22664963, compoundYield 51.2%

Reagents, catalysts & solvents 1

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

Procedure

(S)-tBuBisP*-RuBr2 (16 mg) was placed in a reactor and deaerated. After substitution with argon, a mixture of ethyl 1-(2,4-dichlorobenzoyl)cyclopentanecarboxylate (2.8 g, 5.6 mmol) and methanol-water (101) (30 ml) was added. Under 70° C. and hydrogen pressure (6 kg/cm2), the mixture was stirred for 30 h and concentrated. This was diluted with ethyl acetate (50 ml), washed with water and concentrated to dryness. This was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (0.91 g, 41.3%) as a colorless oil. The enantiomer excess of this product was measured by high performance liquid chromatography (Condition F) and found to be 92%.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. additionThis was diluted with ethyl acetate (50 ml)
  4. washwashed with water
  5. concentrationconcentrated to dryness
  6. customThis was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-5d3735e679f040fa9f08b068ab9c4254
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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