HCID 67661107, compound → (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol

HRID 1599127Notes

Reaction equation

HRID 1599127 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH:12]([CH2:26][OH:27])[CH2:13][C:14]2([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])[OH:17])[CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:27][CH2:26][CH:12]1[CH2:11][CH:10]2[CH:15]([CH2:16][NH:8][CH2:9]2)[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])([OH:17])[CH2:13]1

Participants

4

Reactant 1

HCID 67661107HCID 67661107, compound

Product 1

HCID 67660910(3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-olYield 128.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3.1 g of (3aRS,4RS,6SR,7aSR)-2-benzyl-6-hydroxymethyl-4-(2-methoxyphenyl) perhydroisoindol-4-ol and 0.5 g of 20% palladium hydroxide on carbon black in 75 cm3 of ethanol is hydrogenated under atmospheric pressure at 60° C. for 3 hours. The reaction mixture is subsequently filtered and concentrated to dryness under reduced pressure (2.7 kPa). 3.0 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol are obtained in the form of a thick white foam.

Workup

  1. filtrationThe reaction mixture is subsequently filtered
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-318a7a94667f40deb68390c8e6b56d8a
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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