HCID 10909964, compound → HCID 11745068, compound

HRID 1527820Notes

Reaction equation

HRID 1527820 reaction equation
[C:1]([C@H:4]1[CH2:7][C@@H:6]([CH2:8][CH:9]=[O:10])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]>C1(C)C=CC=CC=1>[OH:10][CH2:9][CH2:8][C@@H:6]1[CH2:7][C@H:4]([C:1](=[O:3])[CH3:2])[C:5]1([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 10909964HCID 10909964, compound

Product 1

HCID 11745068HCID 11745068, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2-((1S,3S)-3-acetyl-2,2-dimethylcyclobutyl)acetaldehyde (8.4 g, 0.05 mol.), 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 98% 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,3S)-3-(2-hydroxyethyl)-2,2-dimethylcyclobutyl)ethanone was obtained in 94% 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-1d858c4edb8e4d00ac78b27f326d0337
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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