HCID 22664981, compound → HCID 22664968, compound

HRID 392598Notes

Reaction equation

HRID 392598 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][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]>CO.O>[OH:5][CH:4]([C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[Cl:1])[C:6]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

3

Reactant 1

HCID 22664981HCID 22664981, compound

Product 1

HCID 22664968HCID 22664968, compoundYield 80.9%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
70 °C

Procedure

tBuBisP*RuBr2 (28 mg) was placed in a reactor and deaerated and substituted with argon. A mixture of deaerated methanol/water (10/1) (33 ml) and ethyl 1-(2-chlorobenzoyl)cyclopentanecarboxylate (3.2 g, 11.4 mmol) was added. Under a hydrogen pressure (6 atm), the mixture was stirred at 70° C. for 7 h and concentrated to dryness. This was dissolved in ethyl acetate, dried over anhydrous sodium sulfate and purified by silica gel column chromatography to give the title compound (2.59 g, yield; 80.9%) as a colorless oil. The enantiomer excess of this product was measured by high performance liquid chromatography (Condition F) and found to be 90% ee.

Workup

  1. additionwas added
  2. concentrationconcentrated to dryness
  3. dissolutionThis was dissolved in ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-de806481858441d6b923044af8681845
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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