HCID 7127533, compound → HCID 60078309, compound

HRID 2085541Notes

Reaction equation

HRID 2085541 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:11][C@@H:12]2[O:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[H][H]>CC(O)C>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:11][C@@H:12]2[O:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7127533HCID 7127533, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 60078309HCID 60078309, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  1. customsynthesized in Example 2
  2. customwas set to 25° C.

Sources & evidence

ORD record
ord-7c25b572dd1f4f0ebc68f4364a4c3f2b
Source dataset
uspto-grants-2004_04
Patent number
US06720439B1

Reaction notes

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