HCID 10998727, compound → HCID 10857224, compound

HRID 1080481Notes

Reaction equation

HRID 1080481 reaction equation
[C:1]1([CH2:7][C:8](=[O:15])[CH:9]([Cl:14])[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(C)C>[Cl:14][C@@H:9]([C@H:8]([OH:15])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 10998727HCID 10998727, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 10857224HCID 10857224, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 200 ml Hastelloy autoclave was put 50 g (GC p=93.2%, 220 mmol) of methyl 4-phenyl-2-chloro-3-oxobutyrate (compound (III)), 99.4 mg (0.055 mmol) of Ru2Cl4 [(R)-T-BINAP]2NEt3, and 100 ml of isopropyl alcohol (IPA) under a nitrogen stream. After heating the solution, a hydrogen pressure of 30 atm was introduced into the autoclave at 100° C. to initiate the reaction. Then, it was confirmed by GC that no unreacted matter remained to complete the reaction (for 1 to 2 hours). IPA was recovered under reduced pressure at not higher than 50° C. to obtain 50.3 g [GC p=92.2%, HPLC o.p. syn 87% (80.5% ee), anti 13% (94.6% ee)] of compound (IV) in a yield of 98.6%.

Workup

  1. temperatureAfter heating the solution
  2. customthe reaction
  3. customthe reaction (for 1 to 2 hours)
  4. customIPA was recovered under reduced pressure at not higher than 50° C.

Sources & evidence

ORD record
ord-3f79d7daa95d4411a65329864eb5cd88
Source dataset
uspto-grants-1996_12
Patent number
US05581007

Reaction notes

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