HCID 67660705, compound → HCID 44213379, compound
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
Product 1
Reagents, catalysts & solvents 2
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.