Diethyl Ether → 2-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

HRID 1780961Notes

Reaction equation

HRID 1780961 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.C([O:14][CH:15]1[CH2:23][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]2[CH:17]([CH2:18][N:19]([CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:20]2)[C:16]1=[O:43])(=O)C.[Cl-].[NH4+].C(OCC)C>O1CCCC1>[CH2:36]([N:19]1[CH2:18][CH:17]2[CH:21]([C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:23][CH:15]([OH:14])[C:16]2([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[OH:43])[CH2:20]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 15183785(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydro-4-isoindoloneHCID 178489560HCID 178489560, compound

Product 1

HCID 193768282-Benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediolYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 84.4 g of 2-methoxyphenylmagnesium bromide in 1000 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 22 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-diphenylperhydro-4-isoindolone in 220 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 18 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution, and taken up with 200 cm3 of diethyl ether and 200 g of ice. 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 crystallized in 250 cm3 of petroleum ether and then recrystallized in 200 cm3 of methanol; the crystals are washed with 200 cm3 of isopropyl ether. 16.4 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol are obtained, melting at 236° C.

Workup

  1. additionis added dropwise, at room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 18 hours
  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. customThe residue is crystallized in 250 cm3 of petroleum ether
  8. customrecrystallized in 200 cm3 of methanol
  9. washthe crystals are washed with 200 cm3 of isopropyl ether

Sources & evidence

ORD record
ord-eedc028c8bdc4146bb046986c7c5d7a6
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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