HCID 53850252, compound → HCID 18396914, compound

HRID 1006661Notes

Reaction equation

HRID 1006661 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:30])([C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]([CH3:29])[N:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[CH2:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:30])([C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]([CH3:29])[N:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 1

HCID 53850252HCID 53850252, compound

Product 1

HCID 18396914HCID 18396914, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of step (i) (2.0 g, 5 mmol) in ethanol (50 ml) was hydrogenated at 50 psi (333 KPa) pressure over 5% palladium on charcoal (0.2 g) for 18 hours at 50° C. A further batch of catalyst (0.2 g) was added, and the hydrogenation was continued for a further 18 hours. The mixture was filtered through Arbocel™ and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica by gradient elution with ethyl acetate/hexane/diethylamine (0:95:5→65:33:2). Fractions containing the desired product were combined and evaporated under reduced pressure. The residue was dissolved and re-evaporated from ethyl acetate (×3) then from ether (×3) to yield a colourless solid. The solid was recrystallised from aqueous ethanol to give the subtitle compound (1.25 g, 62%) as a colourless solid, m.p. 144-145° C., [α]D=−107° (c=0.1%, CH2Cl2, 25° C.).

Workup

  1. filtrationThe mixture was filtered through Arbocel™
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was chromatographed on silica by gradient elution with ethyl acetate/hexane/diethylamine (0:95:5→65:33:2)
  4. additionFractions containing the desired product
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved
  7. customre-evaporated from ethyl acetate (×3)
  8. customfrom ether (×3) to yield a colourless solid
  9. customThe solid was recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-ae698107432c4a5385df01f0969b1da3
Source dataset
uspto-grants-2004_09
Patent number
US06790957B2

Reaction notes

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