HCID 86731810, compound → HCID 86731809, compound

HRID 1527821Notes

Reaction equation

HRID 1527821 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:8][CH2:7][CH2:6][C:5](=[CH2:9])[C@H:4]([CH2:10][CH2:11][C:12](=[O:14])[CH3:13])[C@@H:3]1[CH:15]=[O:16]>C1(C)C=CC=CC=1>[OH:16][CH2:15][C@@H:3]1[C:2]([CH3:17])([CH3:1])[CH2:8][CH2:7][CH2:6][C:5](=[CH2:9])[C@@H:4]1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13]

Participants

3

Reactant 1

HCID 86731810HCID 86731810, compound

Product 1

HCID 86731809HCID 86731809, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

(1S,7R)-2,2-dimethyl-6-methylene-7-(3-oxobutyl)cycloheptanecarbaldehyde (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 50 bars hydrogen. It was then heated to 90° C. and hydrogen pressure was maintained to 30 bars during all the reaction to afford desired product with 92% 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, 4-((1R,2S)-2-(hydroxymethyl)-3,3-dimethyl-7-methylenecycloheptyl) butan-2-one was obtained in 85% yield.

Workup

  1. customequipped with a mechanical stirring device
  2. customSealed autoclave
  3. customwas then purged
  4. temperaturehydrogen pressure was maintained to 30 bars during all
  5. customthe reaction

Sources & evidence

ORD record
ord-42b186d5d7174fb986542cb5d9e3ef5f
Source dataset
uspto-grants-2015_07
Patent number
US09090534B2

Reaction notes

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