HCID 67405299, compound → HCID 67405510, compound

HRID 1372620Notes

Reaction equation

HRID 1372620 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][CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[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][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67405299HCID 67405299, compound

Product 1

HCID 67405510HCID 67405510, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 5-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)-2-pentenoate (1.40 g, 4.22 mmol) and 5% palladium/carbon (wet.) (700 mg) were suspended in methanol (50 ml). Under stirring at room temperature, the resulting suspension was subjected to catalytic hydrogenation at normal pressure for 20 hours. 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: 20 g), whereby from hexane/ethyl acetate (4/1) eluate fractions, the title compound (1.09 g, 78%) 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: 20 g), whereby from hexane/ethyl acetate (4/1) eluate fractions

Sources & evidence

ORD record
ord-a0f4d8c32fd34c66a6de128b4569a4a5
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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