(3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol → (3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol

HRID 55401Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:10]([CH2:11][CH2:12][CH:13]([OH: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>[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])[CH:13]([OH:26])[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 1.5 g of (3aRS,4RS,5RS,7aSR)-2-benzyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol and 120 cm3 of anhydrous ethanol is heated to 60° C. with stirring; 0.49 g of 20% palladium hydroxide on charcoal is added and the reaction mixture is then hydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure. After reaction for 2 hours, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 50 cm3 of isopropyl ether. 1.02 g of (3aRS,4RS,5RS,7aSR)-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 168° C.

Workup

stirringhydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure
customAfter reaction for 2 hours
customthe theoretical volume of hydrogen has been absorbed
filtrationthe reaction mixture is filtered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe residue is crystallized in 50 cm3 of isopropyl ether

Sources & evidence

ORD record: ord-4d899db9016443ecad44fc47bd05fcb1
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Reaction notes

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