HCID 19376828, compound → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

HRID 375448Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[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>C(O)C>[C:33]1([C:11]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:10]3[CH:15]([CH2:16][NH:8][CH2:9]3)[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH:13]([OH:26])[CH2:12]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindole-4,5-diol and 50 cm3 of ethanol is heated at 65° C., while stirring; 0.65 g of 20% strength palladium hydroxide-on-charcoal is added and the reaction mixture is then hydrogenated at a temperature of 65° C. and under atmospheric pressure, while stirring. After a reaction time of 1 hour, the theoretical volume of hydrogen was absorbed; the reaction mixture is filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from 10 cm3 of isopropyl ether. 1.45 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindole-4,5-diol which melts at 230° C. are obtained.

Workup

customis then hydrogenated at a temperature of 65° C. and under atmospheric pressure
stirringwhile stirring
customAfter a reaction time of 1 hour, the theoretical volume of hydrogen was absorbed
filtrationthe reaction mixture is filtered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe residue is crystallized from 10 cm3 of isopropyl ether

Sources & evidence

ORD record: ord-625ff1b8da2c4692a35b61a81dcf2498
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484804

Reaction notes

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