Ammonium Chloride → HCID 67714472, compound

HRID 55411Notes

Reaction equation

HRID 55411 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]([CH3:25])([CH3:24])[CH:21]2[CH:17]([CH2:18][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:20]2)[C:16]1=[O:33])(=O)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH2:26]([N:19]1[CH2:18][CH:17]2[CH:21]([C:22]([CH3:25])([CH3:24])[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:33])[CH2:20]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 67714110(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindoloneHCID 178489560HCID 178489560, compound

Product 1

HCID 67714472HCID 67714472, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 33.8 g of 2-methoxyphenylmagnesium bromide in 75 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 6.6 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone in 75 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. The organic phase is extracted with 3 times 100 cm3 of ethyl ether, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 500 cm3 of petroleum ether. 2.8 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-dimethyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 190° C.

Workup

  1. additionis added dropwise, at room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 15 hours
  3. extractionThe organic phase is extracted with 3 times 100 cm3 of ethyl ether
  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 500 cm3 of petroleum ether

Sources & evidence

ORD record
ord-475038bb2b8a4fef9342ac505496ca28
Source dataset
uspto-grants-1997_04
Patent number
US05624950

Reaction notes

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