HCID 67660705, compound → HCID 44213379, compound

HRID 1599150Notes

Reaction equation

HRID 1599150 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:12][CH:11]2[CH:7]([CH2:8][N:9]([C:13](=[O:29])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21]CC3C=CC=CC=3)[CH2:10]2)[C:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])([OH:30])[CH2:5]1)#[N:2]>C(O)C.[OH-].[OH-].[Pd+2]>[C:1]([CH2:3][CH:4]1[CH2:12][CH:11]2[CH:7]([CH2:8][N:9]([C:13](=[O:29])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])[CH2:10]2)[C:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])([OH:30])[CH2:5]1)#[N:2]

Participants

4

Reactant 1

HCID 67660705HCID 67660705, compound

Product 1

HCID 44213379HCID 44213379, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

0.032 g of 10% palladium hydroxide on carbon is added to a solution of 0.168 g of (3aRS,4RS,6SR,7aSR)-6-cyanomethyl-4-(2-fluorophenyl)-2-(2-benzyloxyphenylacetyl)perhydroisoindol-4-ol in 10 cm3 of absolute ethanol, and then the reaction mixture is hydrogenated at reflux with stirring. After reaction for 4 hours, the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). Trituration in diisopropyl ether gives 0.08 g of (3aRS,4RS,6SR,7aSR)-6-cyanomethyl-4-(2-fluorophenyl)-2-(2-hydroxyphenylacetyl)perhydroisoindol-4-ol in the form of a thick white foam.

Workup

  1. temperatureat reflux
  2. customAfter reaction for 4 hours
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-781e56affcbb47468911f44b74d5ff90
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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