Water → HCID 67719131, compound

HRID 1780975Notes

Reaction equation

HRID 1780975 reaction equation
[C:1]1([C:7]2([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:15]3[CH:11]([CH2:12][N:13]([C:16](=[O:27])[CH2:17][C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=4)[CH2:14]3)[C:10]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])([OH:28])[CH:9]([OH:37])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Cl-].[NH4+]>CO.[Zn]>[C:38]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:27])[CH2:17][C:18]4[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=4)[CH2:14]3)[C:10]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])([OH:28])[CH:9]([OH:37])[CH2:8]2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67719072HCID 67719072, compound

Product 1

HCID 67719131HCID 67719131, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(4-nitrophenyl)acetyl]perhydro-4,5-isoindolediol in 3.3 cm3 of methanol, maintained at a temperature of 50° C., are added 33 cm3 of water, 4.6 g of ammonium chloride and 2.2 g of zinc powder. The reaction mixture is brought to reflux for 30 minutes, cooled to room temperature and then washed with twice 50 cm3 of dichloromethane. The organic phase is separated off after settling, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 70 cm3 of 1N hydrochloric acid. The organic phase is extracted with twice 50 cm3 of ethyl acetate. The aqueous phase is basified with 1N sodium hydroxide and the organic phase is then extracted with 3 times 100 cm3 of ethyl acetate. It is separated off after settling, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The meringue-like product obtained is crystallized in 20 cm3 of isopropyl ether. 0.71 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(4-aminophenyl)acetyl]perhydro-4,5-isoindolediol is obtained, melting at 188° C.

Workup

  1. temperatureto reflux for 30 minutes
  2. washwashed with twice 50 cm3 of dichloromethane
  3. customThe organic phase is separated off
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. extractionThe organic phase is extracted with twice 50 cm3 of ethyl acetate
  8. extractionthe organic phase is then extracted with 3 times 100 cm3 of ethyl acetate
  9. customIt is separated off
  10. dry with materialdried over magnesium sulphate
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  12. customThe meringue-like product obtained
  13. customis crystallized in 20 cm3 of isopropyl ether

Sources & evidence

ORD record
ord-ebb6dfc4c437444cbe1e002b13554768
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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