Lithium Bromide → (3aRS,4RS,6SR,7aSR)-6-bromomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol

HRID 1599160Notes

Reaction equation

HRID 1599160 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([OH:40])[CH2:17][CH:16]([CH2:18]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][CH:14]2[CH:10]1[CH2:11][N:12]([C:29](=[O:39])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH3:38])[CH2:13]2.[Br-:41].[Li+]>CC(C)=O>[Br:41][CH2:18][CH:16]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12]([C:29](=[O:39])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])[CH2:13]2)[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])([OH:40])[CH2:17]1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 86752423(3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol

Product 1

HCID 86752427(3aRS,4RS,6SR,7aSR)-6-bromomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-olYield 65.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.16 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol and 0.345 g of anhydrous lithium bromide in 60 cm3 of acetone is heated at reflux for 18 hours and then concentrated to reduced volume (10 cm3). Following the addition of 20 cm3 of water, the mixture is subjected to extraction with 40 cm3 of ethyl acetate, washed with 20 cm3 of water and then dried over magnesium sulphate. After concentration to dryness under reduced pressure (2.7 kPa), the residue is washed with 20 cm3 of ethyl ether, drained and dried under reduced pressure (2.7 kPa). 0.66 g of (3aRS,4RS,6SR,7aSR)-6-bromomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol is obtained in the form of a white solid. M.p.K =191° C.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated to reduced volume (10 cm3)
  3. additionthe addition of 20 cm3 of water
  4. extractionthe mixture is subjected to extraction with 40 cm3 of ethyl acetate
  5. washwashed with 20 cm3 of water
  6. dry with materialdried over magnesium sulphate
  7. concentrationAfter concentration to dryness under reduced pressure (2.7 kPa)
  8. washthe residue is washed with 20 cm3 of ethyl ether
  9. customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-a7efa51effaa4759a1af3b83b00c3a84
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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