HCID 67404444, compound → HCID 67405408, compound

HRID 1372626Notes

Reaction equation

HRID 1372626 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67404444HCID 67404444, compound

Product 1

HCID 67405408HCID 67405408, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl (E)-6-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)-2-hexenoate (1.90 g, 5.50 mmol) and 5% palladium/carbon (1.0 g) were suspended in methanol (80 ml). The resulting suspension was subjected to catalytic hydrogenation under normal pressure for 19 hours under stirring at room temperature. The catalyst was filtered off and the filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 3 g), whereby from ethyl acetate eluate fractions, the title compound (1.92 g, 100%) was obtained as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe filtrate was distilled under reduced pressure
  3. customto remove the solvent
  4. customThe residue was purified by chromatography on a silica gel column (silica gel: 3 g), whereby from ethyl acetate eluate fractions

Sources & evidence

ORD record
ord-3be0066b0e7b49619893faa64ecad8f7
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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