rel-(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropaneacetaldehyde → HCID 13765715, compound

HRID 1527819Notes

Reaction equation

HRID 1527819 reaction equation
[CH3:1][C:2]1([CH3:12])[C@@H:4]([CH2:5][C:6](=[O:8])[CH3:7])[C@H:3]1[CH2:9][CH:10]=[O:11]>C1(C)C=CC=CC=1>[OH:11][CH2:10][CH2:9][C@@H:3]1[C@H:4]([CH2:5][C:6](=[O:8])[CH3:7])[C:2]1([CH3:12])[CH3:1]

Participants

3

Reactant 1

HCID 10352077rel-(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropaneacetaldehyde

Product 1

HCID 13765715HCID 13765715, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2-((1R,3S)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl)acetaldehyde (8.4 g, 0.05 mol.), to toluene (50 g, 600 wt. %) and (ethylenediamine)[1,2-bis(diphenylphosphino) ethane]ruthenium(bispivalate) (4.8 mg, 0.00625 mmol, 0.0125 mol.%) were loaded altogether in a 125 ml autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 50 bars hydrogen. It was then heated to 90° C. and hydrogen pressure was maintained to 50 bars during all the reaction to afford desired product with 95% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), autoclave was then cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and solvent was removed under vacuum. After flash chromatography, 1-((1S,3R)-3-(2-hydroxyethyl)-2,2-dimethylcyclopropyl)propan-2-one was obtained in 90% yield.

Workup

  1. customequipped with a mechanical stirring device
  2. customSealed autoclave
  3. customwas then purged
  4. temperaturehydrogen pressure was maintained to 50 bars during all
  5. customthe reaction

Sources & evidence

ORD record
ord-ffa6a50af81d401b8225d600f47a016d
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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