HCID 86750864, compound → HCID 22872811, compound

HRID 1780969Notes

Reaction equation

HRID 1780969 reaction equation
[C:1]1([C:7]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@H:15]3[C@H: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>[OH-].[OH-].[Pd+2].C(O)C>[C:43]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C@H:15]3[C@H: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])[C@H:9]([OH:42])[CH2:8]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 1

HCID 86750864HCID 86750864, compound

Product 1

HCID 22872811HCID 22872811, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.5 g of (3aR,4R, SR,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-benzyloxyphenyl)acetyl]perhydro-4,5-isoindolediol and 50 cm3 of ethanol is heated to 60° C. with stirring; 0.5 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 45 minutes, the theoretical volume of hydrogen has been absorbed; the reaction mixture is filtered, followed by concentration to dryness under reduced pressure (2.7 kPa). The meringue-like product obtained is purified by crystallization in 10 cm3 of isopropyl ether to give 1.09 g of (3aR,4R,5R,7aR)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-hydroxyphenyl)acetyl]perhydro-4,5-isoindolediol, melting at 188° C.

Workup

  1. stirringhydrogenated, with stirring, at a temperature of 60° C. and at atmospheric pressure
  2. customAfter reaction for 45 minutes
  3. customthe theoretical volume of hydrogen has been absorbed
  4. filtrationthe reaction mixture is filtered
  5. concentrationfollowed by concentration to dryness under reduced pressure (2.7 kPa)
  6. customThe meringue-like product obtained
  7. customis purified by crystallization in 10 cm3 of isopropyl ether

Sources & evidence

ORD record
ord-50951ff0bd514fd4ae9a987c41fc417e
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

Loading…