3-(Dimethylamino)-1-phenyl-1-propanone → HCID 853890, compound

HRID 2085542Notes

Reaction equation

HRID 2085542 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[H][H]>CC(O)C>[C:7]1([C@H:5]([OH:6])[CH2:4][CH2:3][N:2]([CH3:13])[CH3:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 770423-(Dimethylamino)-1-phenyl-1-propanone2×HCID 178418361HCID 178418361, compound

Product 1

HCID 853890HCID 853890, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Chiral hydrogenation of 3-(dimethylamino)propiophenone was carried out (see formula (13) below). That is, a reaction was carried out in accordance with the procedures of Example 4 using the (S,SS)-ruthenium hydride complex synthesized in Example 2 and using 3-(dimethylamino)propiophenone(886 mg; 5.0 mmol) as the substrate and 2-propanol (5 mL) as the solvent. However, the hydrogen pressure was set to 8 atmosphere, the reaction temperature was set to 250° C., and the reaction time was set to 12 hours. As a result, (R)-1-phenyl-3-(dimethylamino)propane-1-ol was obtained at a conversion rate of 100%, isolation yield of 89% (796 mg; 4.45 mmol), and enantiomeric excess of 97%. HPLC (column: CHIRALCEL OD; size: 4.6 mm×250 mm; made by Daicel Chemical Industries Ltd.; solvent: 9:1 hexane/2-propanol; temperature: 30° C.; UV wavelength: 254 nm; flow rate: 0.5 ml/minute; tR of (R)-1-phenyl-3-(dimethylamino)propane-1-ol: 14.4 minutes (98.4%); tR of S alcohol: 20.4 minutes (1.6%)); [α]26D+31.8° (c: 1.67; CH3OH); absolute structure: R; literature value: [α]D+27.6° (c:1.61; CH3OH),(R).

Workup

  1. customwas set to 250° C.

Sources & evidence

ORD record
ord-dd1ff33e524d4f79acec90d9d6f4f84c
Source dataset
uspto-grants-2004_04
Patent number
US06720439B1

Reaction notes

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