HCID 67462724, compound → HCID 11552864, compound

HRID 554573Notes

Reaction equation

HRID 554573 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[CH2:11][C@:10]1([C:41]1[CH:46]=[C:45]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([CH2:54][CH3:55])=[CH:50][CH:49]=2)[CH:44]=[CH:43][C:42]=1[F:56])[OH:40])C1C=CC=CC=1>CO.C1COCC1.[OH-].[Pd+2].[OH-]>[CH2:54]([C:51]1[CH:50]=[CH:49][C:48]([CH2:47][C:45]2[CH:44]=[CH:43][C:42]([F:56])=[C:41]([C@:10]3([OH:40])[CH2:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]3[OH:8])[CH:46]=2)=[CH:53][CH:52]=1)[CH3:55]

Participants

4

Reactant 1

HCID 67462724HCID 67462724, compound

Product 1

HCID 11552864HCID 11552864, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a mixture solution of (1R,2R,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethyl-1-[5-(4-ethylbenzyl)-2-fluorophenyl]cyclohexanol (271 mg, 0.361 mmol) in methanol-THF (1:1) mixed solvent (20 mL), a 20% palladium hydroxide catalyst (40 mg) was added thereto. The mixture was stirred under a hydrogen atmosphere for 30 minutes, and then the catalyst was filtered off. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:10)] to obtain the title compound (44.6 mg, 31.6%).

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationThe solvent was distilled under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:10)]

Sources & evidence

ORD record
ord-2663289fe0e54c05b024d1e8505e6c1a
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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