HCID 57231691, compound → HCID 57026459, compound

HRID 2289382Notes

Reaction equation

HRID 2289382 reaction equation
C([O:8][C@@H:9]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C@@H:11]([F:20])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])C1C=CC=CC=1>[Pd].CO>[F:20][C@H:11]([CH2:10][C@@H:9]([OH:8])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14]

Participants

4

Reactant 1

HCID 57231691HCID 57231691, compound

Product 1

HCID 57026459HCID 57026459, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 200 ml flask were charged 60 ml of methanol, 3.18 g of 10% palladium-on-carbon, and 10.6 g of t-butyl (3R,5S)-5-benzyloxy-3-fluorononanoate obtained in Step 4, and hydrogenolysis was conducted at room temperature for 8 hours. The catalyst was removed by filtration, and the filtrate was distilled to remove the solvent. The residue was purified by silica gel column chromatography to obtain 5.0 g (64.2%) of the titled compound.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe filtrate was distilled
  3. customto remove the solvent
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9cd4dd4080654088b66f7471df2a6832
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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