(3aRS,4RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4-perhydroisoindolol → (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-4-perhydroisoindolol

HRID 55398Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 16 g of (3aRS,4RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4-perhydroisoindolol and 200 cm3 of anhydrous ethanol is heated at 60° C. with stirring; 2 g of 20% palladium hydroxide on charcoal are added and the reaction mixture is then hydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure. After reaction for 6 hours the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). 5.72 g of (3aRS,4RS,7aSR)-4-(2-methoxyphenyl)-4-perhydroisoindolol are obtained in the form of a cream-coloured foam.

Workup

stirringhydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure
customAfter reaction for 6 hours the reaction mixture
filtrationis filtered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-f5dc8ac154d544cd87f0187fb73f0f9c
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Reaction notes

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