HCID 19047651, compound → HCID 19047654, compound

HRID 375450Notes

Reaction equation

HRID 375450 reaction equation
[C:1]1([C:7]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:15]3[CH:11]([CH2:12][N:13]([C:16](=[O:32])[CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[O:24]CC4C=CC=CC=4)[CH2:14]3)[C:10]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][CH3:41])([OH:33])[CH:9]([OH:42])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C>[C:43]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:15]3[CH:11]([CH2:12][N:13]([C:16](=[O:32])[CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[OH:24])[CH2:14]3)[C:10]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][CH3:41])([OH:33])[CH:9]([OH:42])[CH2:8]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

3

Reactant 1

HCID 19047651HCID 19047651, compound

Product 1

HCID 19047654HCID 19047654, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.5 g of (3aRS, 4RS, 5RS, 7aRS )-7,7-diphenyl-4-(2-methoxyphenyl )-2-[(2-benzyloxyphenyl)acetyl]perhydroisoindole-4,5-diol and 50 cm3 of ethanol is heated at 60° C. while stirring; 0.5 g of 20% strength palladium hydroxide-on-charcoal is added and the reaction mixture is then hydrogenated at a temperature of 60° C. and under atmospheric pressure, while stirring. After a reaction time of 45 minutes, 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 20 cm3 of isopropyl ether. 0.8 g of (3aRS, 4RS, 5RS, 7aRS ) -7,7-diphenyl-4- (2-methoxyphenyl )-2-[(2-hydroxyphenyl)acetyl] perhydroisoindole-4,5-diol which melts at 188°-190° C. is obtained.

Workup

  1. customis then hydrogenated at a temperature of 60° C. and under atmospheric pressure
  2. stirringwhile stirring
  3. customAfter a reaction time of 45 minutes, the theoretical volume of hydrogen was absorbed
  4. filtrationthe reaction mixture is filtered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized from 20 cm3 of isopropyl ether

Sources & evidence

ORD record
ord-5cb1f2dc03964002b98c6039071caa5e
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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