HCID 59006381, compound → HCID 59006355, compound

HRID 2378949Notes

Reaction equation

HRID 2378949 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:9]1=[O:26].[H][H]>CO.[Pt](=O)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH2:14]2)[C:9]1=[O:26]

Participants

5

Reactant 2

HCID 59006381HCID 59006381, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59006355HCID 59006355, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

tert-Butyl 4-(3-(2-fluorophenyl)-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate (530 mg, 1.5 mmol) was dissolved in methanol (25 mL). Platinum(IV) oxide (28 mg, 123.3 Emoles) was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 60 psi of hydrogen gas. Reaction shook at room temperature for 4 hours. More platinum(IV) oxide (28 mg, 123.3 μmol) was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 60 psi of hydrogen gas. Reaction shook at room temperature for 18 hours. Mixture was removed from the apparatus and then filtered over celite. The filtrate was concentrated by roto-vap. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as clear colorless oil in 45% yield. MS (M−C4H10O+H)+=290.0.

Workup

  1. customReaction vessel
  2. customReaction
  3. customReaction vessel
  4. customReaction
  5. stirringshook at room temperature for 18 hours
  6. customMixture was removed from the apparatus
  7. filtrationfiltered over celite
  8. concentrationThe filtrate was concentrated by roto-vap
  9. washSilica gel chromatography eluting ethyl acetate-hexanes

Sources & evidence

ORD record
ord-97b7096a597a459d97cf48262edbf937
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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