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