(E)-3-Nonen-2-one → HCID 5367540, compound

HRID 2085543Notes

Reaction equation

HRID 2085543 reaction equation
[CH3:1][C:2](=[O:10])/[CH:3]=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H][H]>CC(O)C>[CH3:1][CH:2]([OH:10])/[CH:3]=[CH:4]/[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 5317045(E)-3-Nonen-2-one2×HCID 178418361HCID 178418361, compound

Product 1

HCID 5367540HCID 5367540, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Chiral hydrogenation of (E)-3-nonene-2-one was carried out(see formula (14) 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 (E)-3-nonene-2-one (701 mg; 5.0 mmol) (made by Tokyo Kasei Kogyo Co., Ltd.)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 16 hours. As a result, (E)-3-nonene-2-ol was obtained at a GC yield of 95%, isolation yield of 93% (668 mg; 4.65 mmol), and enantiomeric excess of 99%. GC (column: Chirasil-DEX CB; column temperature: 65° C.; injection and detection temperature: 200° C.; helium pressure: 41 kPa; tR of (R)-(E)-3-nonene-2-ol: 70.5 minutes(99.6%); tR of (S)-(E)-3-nonene-2-ol:80.7 minutes (0.4%)); [α]26D+21.16° (c:1.042; CHCl3); absolute structure: R; literature value: [α]25D+10.68° (c:1.03; CHCl3), 97% ee (R).

Workup

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

Sources & evidence

ORD record
ord-5ebe2aac054f4a80a4454e9f4f25d60c
Source dataset
uspto-grants-2004_04
Patent number
US06720439B1

Reaction notes

Loading…