HCID 7127533, compound → HCID 60078309, compound

Participants

Reaction Steps

Chiral hydrogenation of (R)-glycidyl 3-acetylphenyl ether was carried out (see formula (12) below). That is, a reaction was carried out in accordance with the procedures of Example 4 using the (S,SS)-ruthenium hydride complex (1.5 mg; 0.00125 mmol) synthesized in Example 2 and using (R)-glycidyl 3-acetylphenyl ether (481 mg; 2.5 mmol) as the substrate and 2-propanol (2.5 mL) as the solvent. However, the hydrogen pressure was set to 8 atmosphere, the reaction temperature was set to 25° C., and the reaction time was set to 14 hours. As a result, one of the stereoisomers of (R)-glycidyl 3-(1-hydroxyethyl)phenyl ether was obtained at a conversion rate of 99%, isolation yield of 98% (475 mg; 2.45 mmol), and enantiomeric excess of 99%. GC (column: Chirasil-DEX CB; column temperature: 135° C.; injection and detection temperature: 250° C.; helium pressure: 60 kPa; tR of (R)-glycidyl (R) or (S)-3-(1-hydroxyethyl)phenyl ether: 94.9 minutes (98.6%); tR of the stereoisomers: 109.6 minutes (0.5%); tR of (R)-glycidyl 3-acetylphenyl ether: 46.5 minutes (0.9%); [α]29D: +32.0° (c: 1.36; CHCl3); The absolute structure was not determined.

Provenance & Evidence