HCID 67460266, compound → HCID 11689581, compound

HRID 554569Notes

Reaction equation

HRID 554569 reaction equation
[CH2:1]([C:3]1[CH:56]=[CH:55][C:6]([CH2:7][C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:19][C@H:18]([CH2:20][O:21]CC4C=CC=CC=4)[C@@H:17]([O:29]CC4C=CC=CC=4)[C@H:16]([O:37]CC4C=CC=CC=4)[C@H:15]3[O:45]CC3C=CC=CC=3)[CH:11]=[CH:10][C:9]=2[O:53][CH3:54])=[CH:5][CH:4]=1)[CH3:2]>C1COCC1.CO.[OH-].[Pd+2].[OH-]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:19][C@H:18]([CH2:20][OH:21])[C@@H:17]([OH:29])[C@H:16]([OH:37])[C@H:15]3[OH:45])[CH:11]=[CH:10][C:9]=2[O:53][CH3:54])=[CH:55][CH:56]=1)[CH3:2]

Participants

5

Reactant 1

HCID 67460266HCID 67460266, compound

Product 1

HCID 11689581HCID 11689581, compoundYield 77.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-ethylbenzyl)-1-methoxy-4-[(1S,2S,3R,4R,5R)-2,3,4-tris-benzyloxy-5-(benzyloxymethyl)cyclohexyl]benzene (10 mg, 0.013 mmol) in THF (0.2 mL) and methanol (1 mL), a 20% palladium hydroxide catalyst (10 mg) was added and the mixture was stirred under a hydrogen atmosphere at room temperature for 13 hours. After filtering the catalyst, the filtrate was concentrated under reduced pressure. The obtained residue was purified by preparative TLC [developing solution=methanol:methylene chloride (1:10)] to obtain the title compound (3.9 mg, 75%).

Workup

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

Sources & evidence

ORD record
ord-12a03361f874477f8319333b2fb1d02e
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

Loading…