HCID 86697227, compound → HCID 86697226, compound

HRID 237565Notes

Reaction equation

HRID 237565 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]3[C:8]=2[CH2:9][CH2:10][C:11]3=[O:17])[CH2:3][CH2:2]1>O1CCCC1.[Pd]>[F:16][C:13]1[CH:14]=[CH:15][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[C:8]2[C:12]=1[C:11](=[O:17])[CH2:10][CH2:9]2

Participants

4

Reactant 1

HCID 86697227HCID 86697227, compound

Product 1

HCID 86697226HCID 86697226, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3,6-dihydro-2H-pyran-4-yl)-7-fluoro-2,3-dihydro-1H-inden-1-one (100 mg) in tetrahydrofurane (10 mL) is added 10% palladium on activated carbon (30 mg) and the mixture is hydrogenated at a pressure of 2 bar for 12 hours. The catalyst is filtered off and washed with methanol. The combined mother liquors are concentrated and the residue is chromatographed on silica gel (petrole ether/ethyl acetate 80:20→50:50) to give the title compound. Yield: 55 mg; LC (method 8): tR=0.36 min; Mass spectrum (ESI+): m/z=339 [M+H]+.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with methanol
  3. concentrationThe combined mother liquors are concentrated
  4. customthe residue is chromatographed on silica gel (petrole ether/ethyl acetate 80:20→50:50)

Sources & evidence

ORD record
ord-b2c5a642f3c945259a9d9386746d8290
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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