HCID 13417622, compound → HCID 60078307, compound
Reaction equation
[O:1]=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].[H][H]>CC(O)C>[OH:1][C@@H:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Chiral hydrogenation of methyl 7-oxo-7-phenylheptanoate was carried out (see formula (11) 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 methyl 7-oxo-7-phenylheptanoate (587 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 12 hours. As a result, methyl (R)-7-hydroxy-7-phenylheptanoate was obtained at a conversion rate of 100%, isolation yield of 98% (588 mg; 2.48 mmol), and enantiomeric excess of 95%. The enantiomeric excess was determined by HPLC analysis of the corresponding benzoic acid ester. HPLC (column: CHIRALPAC AD: size: 4.6 mm×250 mm; made by Daicel Chemical Industries Ltd.; solvent: hexane/2-propanol=19:1; temperature: 30° C.; UV wavelength: 254 nm; flow rate: 0.5 ml/minute; tR of methyl (R)-7-benzoyloxy-7-phenylheptanoate: 20.8 minutes (97.6%); tR of the Sisomer:25.9 minutes(2.4%)); [α]28D+29.1° (c:1.09;CHCl3); absolute structure: R. The absolute structure was determined from the value of the angle of rotation of 1-phenylheptanol obtained by conversion.
Workup
- customsynthesized in Example 2
- customwas set to 25° C.
Sources & evidence
- ORD record
- ord-b3b0245de5a9464db702437dddbe27bf
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06720439B1
Reaction notes
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