2-Cyclopenten-1-one → HCID 10376463, compound

HRID 916298Notes

Reaction equation

HRID 916298 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[CH3:7][CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10]>CC(O)(C)C>[CH3:12][O:11][C:9]([C:8]([CH:3]1[CH2:4][CH2:5][C:1](=[O:6])[CH2:2]1)([C:13]([O:15][CH3:16])=[O:14])[CH3:7])=[O:10]

Participants

4

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 69104Dimethyl methylmalonate

Product 1

HCID 10376463HCID 10376463, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

Under an atmosphere of argon, 12.6 mg (0.02 mmol, S/C=50) of Ru[(S,S)-Tsdpen] (hexamethylbenzene), 84 μL (1.0 mmol) of 2-cyclopentenone, 133 μL (1.0 mmol) of dimethyl methylmalonate, and 1 mL of 2-methyl-2-propanol were placed in a 20 mL Schlenk tube and stirred at 40° C. for 24 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 54 mg (24% yield) of the title compound. The optical purity was measured by HPLC (CHIRALPAK AS manufactured by Daicel Chemical Industries, Ltd., hexane: 2-propanol=80:20, flowrate 1.5 mL/min, detection at 210 nm) and it was found to be 76% ee.

Workup

  1. customThis solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)

Sources & evidence

ORD record
ord-994ed131dbf84ab798d25d1946521013
Source dataset
uspto-grants-2007_09
Patent number
US07268250B2

Reaction notes

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