(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-5methyl-4-perhydroisoindolol → 4-(2-Methoxyphenyl)-5-methyl-4-perhydroisoindolol

HRID 55418Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH:13]([CH3:26])[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]>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:14]1([OH:17])[CH:13]([CH3:26])[CH2:12][CH2:11][CH:10]2[CH:15]1[CH2:16][NH:8][CH2:9]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of I g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-5-methyl-4-perhydroisoindolol in 15 cm3 of anhydrous ethanol are added 2 g of 20% palladium hydroxide on charcoal and the reaction mixture is then hydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure. After reaction for 1 hour, the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). 0.74 g of (3aRS,4RS, 5RS, 7aSR)-4-(2-methoxyphenyl)-5-methyl-4-perhydroisoindolol is obtained in the form of a yellow foam.

Workup

customAfter reaction for 1 hour
filtrationthe reaction mixture is filtered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-67a1b9906df3438f954f31968b9b5ac4
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Reaction notes

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