HCID 10838167, compound → HCID 10504686, compound

HRID 1489444Notes

Reaction equation

HRID 1489444 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:33])([CH2:31][OH:32])[C@H:9]([N:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:18][CH:17]=2)[C:12]1=[O:30])[CH3:10]>C(O)(=O)C.[C].[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:33])([CH2:31][OH:32])[C@H:9]([N:11]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:26])[F:27])=[CH:18][CH:17]=2)[C:12]1=[O:30])[CH3:10]

Participants

4

Reactant 1

HCID 10838167HCID 10838167, compound

Product 1

HCID 10504686HCID 10504686, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-[(1R,2S)-2-(2-fluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (1.0 g) in acetic acid (15 ml) was hydrogenated over 10% palladium carbon (50% wet, 0.25 g) under ordinary pressure for 5 hours at room temperature and then 3 hours at 50° C. After cooling, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was recrystallized from diisopropyl ether to give 1-[(1R,2S)-2-(2-fluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-imidazolidinone (0.69 g) as a colorless crystalline powder. The mother liquor was concentrated in vacuo and the residue was purified by chromatography on silica gel (eluent; hexane-ethyl acetate, 2:1) followed by crystallization from a mixture of diisopropyl ether and hexane to give the additional product (0.20 g).

Workup

  1. custom3 hours
  2. customat 50° C
  3. temperatureAfter cooling
  4. filtrationthe catalyst was filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-eda9b4842d754cbab2a79628deabc646
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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