(3aRS,4RS,7SR,7aRS)-2-benzyl-7-(hydroxymethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol → (3aRS,4RS,7SR,7aRS)-7-(hydroxymethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol

HRID 55424Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([CH2:27][OH:28])([CH3:26])[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>[OH:28][CH2:27][C:11]1([CH3:26])[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][CH2:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3.5 g of (3aRS,4RS,7SR,7aRS)-2-benzyl-7-(hydroxymethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol, 2.0 g of 20% palladium hydroxide on charcoal and 75 cm3 of ethanol is heated to 50° C. After sparging with hydrogen for two hours, the reaction mixture is cooled to room temperature and flushed with a stream of nitrogen, filtered and concentrated under reduced pressure (2.7 kPa). 1.5 g of (3aRS,4RS,7SR,7aRS)-7-(hydroxymethyl)-4-(2-methoxyphenyl)-7-methyl-4-perhydroisoindolol are obtained in the form Of a white solid.

Workup

customAfter sparging with hydrogen for two hours
temperaturethe reaction mixture is cooled to room temperature
customflushed with a stream of nitrogen
filtrationfiltered
concentrationconcentrated under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-54bf36ceb0254d35a41c0b8e95935ae4
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Reaction notes

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