Sodium Chloride → Perhydroisoindole-4,5-diol

HRID 375447Notes

Reaction equation

HRID 375447 reaction equation
O.[OH:2]N1C2C=CC=CC=2N=N1.CN(C)[CH2:14][CH2:15][CH2:16][N:17]=[C:18]=NCC.C(N(C(C)C)CC)(C)C.C[O:33][C:34]1C=C[CH:37]=[CH:36][C:35]=1[C@H](C)C(O)=O.[Cl-].[Na+]>ClCCl.O>[CH2:16]1[CH:15]2[CH:14]([CH:34]([OH:33])[CH:35]([OH:2])[CH2:36][CH2:37]2)[CH2:18][NH:17]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acid

Product 1

HCID 18994337Perhydroisoindole-4,5-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

30 mg of 1-hydroxybenzotriazole hydrate, 0.66 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 0.6 cm3 of diisopropylethylamine are added to a solution of 1.1 g of (3AS,4S,5S,7AS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindole-4,5-diol and 0.58 g of (S)-2-(2-methoxyphenyl)propanoic acid in 30 cm3 of dichloromethane, cooled to 0° C. The mixture is stirred at room temperature for 3 hours and 30 minutes and 100 cm3 of water and 50 cm3 of an aqueous saturated solution of sodium chloride are added. The organic phase is decanted, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The yellow residue obtained is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm) by eluting under a nitrogen pressure of 50 kPa with a mixture of cyclohexane and ethyl acetate (60/40 by volume) and collecting fractions of 25 cm3. Fractions 6 to 14 are combined and then concentrated to dryness under reduced pressure (2.7 kPa). 0.9 g of (3AS,4S,5S,7AS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[S)- 2-(2methoxyphenyl)propionyl]perhydroisoindole-4,5-diol which melts at 256° C. is obtained.

Workup

  1. customThe organic phase is decanted
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe yellow residue obtained
  5. customis chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2 cm, height 30 cm)
  6. washby eluting under a nitrogen pressure of 50 kPa
  7. additionwith a mixture of cyclohexane and ethyl acetate (60/40 by volume)
  8. customcollecting fractions of 25 cm3
  9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-6886ebf148784daba51a68de0b2d68d1
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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