HCID 12187278, compound → HCID 12097073, compound

HRID 1527822Notes

Reaction equation

HRID 1527822 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:5][C@H:4]([C:6](=[CH2:11])[CH2:7][CH2:8][CH:9]=[O:10])[C@H:3]1[CH2:12][CH2:13][C:14](=[O:16])[CH3:15]>C1(C)C=CC=CC=1>[OH:10][CH2:9][CH2:8][CH2:7][C:6]([C@@H:4]1[C@@H:3]([CH2:12][CH2:13][C:14](=[O:16])[CH3:15])[C:2]([CH3:17])([CH3:1])[CH2:5]1)=[CH2:11]

Participants

3

Reactant 1

HCID 12187278HCID 12187278, compound

Product 1

HCID 12097073HCID 12097073, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

4-((1S,2R)-3,3-dimethyl-2-(3-oxobutyl)cyclobutyl)pent-4-enal (11.8 g, 0.05 mol.), toluene (70.8 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 200 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 20 bars hydrogen. It was then heated to 90° C. and hydrogen pressure was maintained to 20 bars during all the reaction to afford desired product with 95% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), to 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, 4-((1R,4S)-4-(5-hydroxypent-1-en-2-yl)-2,2-dimethylcyclobutyl)butan-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 20 bars during all
  5. customthe reaction

Sources & evidence

ORD record
ord-81211de11d714e068217cacfaaa3e785
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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