ChemicalBook CAS DataBase List (R)-(-)-MUSCONE

(R)-(-)-MUSCONE synthesis

10synthesis methods

Product Name:(R)-(-)-MUSCONE
CAS Number:10403-00-6
Molecular formula:C16H30O
Molecular Weight:238.41

2-Cyclopentadecen-1-one, 3-methyl-, (2Z)-

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Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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Yield: 86 % ee

Reaction Conditions:

with hydrogen;Ru₂Cl₄[(R)Tol-BINAP]2(NEt₃) in methanol at 25; under 36778.6 Torr; for 24 h;Inert atmosphere;

Steps:

7
Put in a 100 ml pressure vessel filled with nitrogen were 2g of (Z)-3-methyl-2-cyclopentadecenone that was a fraction obtained in Example 6 described above, 10 mg of Ru₂Cl₄[(R)Tol-BINAP]₂(NEt₃) serving as the optically active ruthenium complex catalyst, and 15 ml of methanol serving as a solvent. The mixture was then subjected to agitation for 24 hours at 25°C under pressurized hydrogen of 50 kg/cm², thereby performing asymmetric hydrogenation. After the reaction was completed, the methanol, which was used as the solvent, was removed by distillation. Thereafter, 1.9g of (R)-muscone, which is optically active muscone, was obtained by purifying the resulting crude reaction product by means of silica gel column chromatography. A liquid chromatography analysis of this (R)-muscone indicated that the ratio of (R)- and (S)-isomers was 93:7.

References:

Doya, Masaharu EP2412696, 2012, A1 Location in patent:Page/Page column 9

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References

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References

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References