Ammonium Chloride → HCID 67736913, compound

HRID 375451Notes

Reaction equation

HRID 375451 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].[C:10]1([C:16]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:24]3[CH:20]([CH2:21][NH:22][CH:23]3[C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:19](=[O:34])[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[C:27]1([CH2:26][C:25]([CH:23]2[CH:24]3[CH:20]([C:19]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([OH:34])[CH2:18][CH2:17][C:16]3([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:21][NH:22]2)=[O:33])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 67736934HCID 67736934, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 67736913HCID 67736913, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of phenylmagnesium bromide (prepared starting from 3.14 g of bromobenzene and 0.48 [lacuna] of magnesium in 30 cm3 of ether) is added to a suspension of 4.09 g of (3aRS,7aRS)-7,7-diphenyl-2-phenylacetylperhydroisoindol-4-one in 50 cm3 of tetrahydrofuran. The reaction mixture is stirred at 25° C. for 1 hour and then heated under reflux for 2.5 hours, cooled and treated with 150 cm3 of a saturated solution of ammonium chloride. The organic phase is washed with water (2×100 cm3). The aqueous phases are extracted with 100 cm3 of ethyl acetate. The combined organic phases are washed with 100 cm3 of a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 30 cm3 of acetonitrile to give 2.9 g of (3aRS,4RS,7aRS)-2-phenylacetyl- 4,7,7-triphenylperhydroisoindol-4-ol in the form of white crystals which melt at 270° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. temperaturecooled
  4. washThe organic phase is washed with water (2×100 cm3)
  5. extractionThe aqueous phases are extracted with 100 cm3 of ethyl acetate
  6. washThe combined organic phases are washed with 100 cm3 of a saturated solution of sodium chloride
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customThe residue is crystallized in 30 cm3 of acetonitrile

Sources & evidence

ORD record
ord-f95ebe51fce54c48a82dd45293f08449
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

Loading…