HCID 67460491, compound → HCID 11553111, compound

HRID 554572Notes

Reaction equation

HRID 554572 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[O:56][CH2:57][CH3:58])O)C1C=CC=CC=1>C1COCC1.CO.[OH-].[Pd+2].[OH-]>[CH2:57]([O:56][C:42]1[CH:43]=[CH:44][C:45]([CH2:47][C:48]2[CH:49]=[CH:50][C:51]([CH2:54][CH3:55])=[CH:52][CH:53]=2)=[CH:46][C:41]=1[C@@H:10]1[CH2:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]1[OH:8])[CH3:58]

Participants

5

Reactant 1

HCID 67460491HCID 67460491, compound

Product 1

HCID 11553111HCID 11553111, compoundYield 20.3%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the (1S,2R,3S,4R,5R)-2,3,4-tris-benzyloxy-5-benzyloxymethyl-1-[2-ethoxy-5-(4-ethylbenzyl)-phenyl]cyclohexanol (402 mg, 0.517 mmol) in THF (4 ml) and methanol (2 mL) as obtained in Example 67, a 20% palladium hydroxide catalyst (78 mg) was added and the mixture solution was stirred under a hydrogen atmosphere for 19 hours. After filtering the catalyst, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (10:1)] to obtain the title compound (42 mg, 20%).

Workup

  1. filtrationAfter filtering the catalyst
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (10:1)]

Sources & evidence

ORD record
ord-1c56a1cac80c4398ab9f94e97e44cec7
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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