HCID 68089123, compound → HCID 66867975, compound

HRID 1631878Notes

Reaction equation

HRID 1631878 reaction equation
C([O:8][CH:9]1[CH2:14][CH2:13][CH:12](/[CH:15]=[C:16]2/[C:17](=[O:37])[CH:18]([C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])[CH:19]([O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:20]/2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH:16]2[CH2:20][CH:19]([O:21][C:22](=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24])[CH:18]([C:28]3[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=3[CH3:36])[C:17]2=[O:37])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 68089123HCID 68089123, compound

Product 1

HCID 66867975HCID 66867975, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 2,2-dimethyl-propionic acid 4-[1-(4-benzyloxy-cyclohexyl)-meth-(E)-ylidene]-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester (4.5 g, 9.0 mmol) is dissolved in ethyl acetate (40 ml), 1 g of 5% palladium on carbon is added and the reaction mixture is placed under hydrogen pressure (3 bars) for 3 hours. The reaction mixture is filtered and washed with ethyl acetate. The filtrate is absorbed onto silica gel and purified by flash chromatography to give a sticky solid. The solid was crystallised from hexane to give 2,2-dimethyl-propionic acid 4-(4-hydroxy-cyclohexylmethyl)-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester (1.37 g).

Workup

  1. customfor 3 hours
  2. filtrationThe reaction mixture is filtered
  3. washwashed with ethyl acetate
  4. customThe filtrate is absorbed onto silica gel
  5. custompurified by flash chromatography
  6. customto give a sticky solid
  7. customThe solid was crystallised from hexane

Sources & evidence

ORD record
ord-8015ac90b1024a199fbe0fd4686733ef
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

Loading…