HCID 67406569, compound → HCID 67406325, compound

HRID 1372625Notes

Reaction equation

HRID 1372625 reaction equation
C([O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][O:13][CH2:14][C@@H:15]1[CH2:19][C@H:18]([F:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[C:24]([O:23][C:21]([N:16]1[CH2:17][C@@H:18]([F:20])[CH2:19][C@H:15]1[CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 67406569HCID 67406569, compound

Product 1

HCID 67406325HCID 67406325, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

In ethanol (200 ml) were suspended (Z)-(2S,4S)-2-(4-benzyloxy-2-butenyloxymethyl)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine (4.58 g, 12.1 mmol) and 20% palladium hydroxide (4.0 g). The resulting suspension was subjected to catalytic hydrogenation at room temperature under normal pressure for 14 hours. The catalyst was then 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: 100 g), whereby from chloroform/acetone (10/1) eluate fractions, the title compound (2.42 g, 67%) was obtained as a colorless oil.

Workup

  1. filtrationThe catalyst was then 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: 100 g), whereby from chloroform/acetone (10/1) eluate fractions

Sources & evidence

ORD record
ord-1241dc4f90d44816bd17b9d4d852b94a
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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