HCID 58003045, compound → HCID 58003015, compound

HRID 1516725Notes

Reaction equation

HRID 1516725 reaction equation
[C:1]1([C:6]2[C:18]([CH:19]([OH:30])[C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[C:17]([CH:31]([CH3:33])[CH3:32])[CH:16]=[C:15]3[C:7]=2[C:8](=[O:34])[CH2:9][C:10]2([O:14]3)[CH2:13][CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Rh]>[CH:1]1([C:6]2[C:18]([CH:19]([OH:30])[C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=3)=[C:17]([CH:31]([CH3:32])[CH3:33])[CH:16]=[C:15]3[C:7]=2[C:8](=[O:34])[CH2:9][C:10]2([O:14]3)[CH2:11][CH2:12][CH2:13]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 58003045HCID 58003045, compound

Product 1

HCID 58003015HCID 58003015, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

63 mg (0.031 mmol) of rhodium-on-carbon (5%) are added to a solution of 289 mg (0.61 mmol) of rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropylspiro[chromen-2,1′-cyclobutan]-4(3H)-one (Example 62A) in 10 ml of ethanol, and the mixture is hydrogenated under a hydrogen pressure of 60 bar at room temperature for 18 h. For work-up, the suspension is filtered through kieselguhr, the filter cake is washed with ethyl acetate and the filtrate is concentrated under reduced pressure. The residue is taken up in 10 ml of ethanol, the same amount of rhodium-on-carbon is added again and the mixture is hydrogenated under a hydrogen pressure of 60 bar at room temperature for a further 18 h. The suspension is again filtered through kieselguhr, the filter cake is washed with ethyl acetate and the filtrate is concentrated under reduced pressure. The crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 15:1).

Workup

  1. customat room temperature
  2. customfor 18 h
  3. filtrationFor work-up, the suspension is filtered through kieselguhr
  4. washthe filter cake is washed with ethyl acetate
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. additionthe same amount of rhodium-on-carbon is added again
  7. customat room temperature
  8. customfor a further 18 h
  9. filtrationThe suspension is again filtered through kieselguhr
  10. washthe filter cake is washed with ethyl acetate
  11. concentrationthe filtrate is concentrated under reduced pressure
  12. customThe crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 15:1)

Sources & evidence

ORD record
ord-4d6d7a8e35954cc68f06b8fa38ba64a5
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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