Hydrochloric Acid → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(3-indolylacetyl)-perhydroisoindole-4,5-diol

HRID 2211428Notes

Reaction equation

HRID 2211428 reaction equation
CN(C)CCCN=C=NCC.C(NC(C)C)(C)C.Cl.[C:20]1([C:26]2([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:34]3[CH:30]([CH2:31][NH:32][CH2:33]3)[C:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])([OH:35])[CH:28]([OH:44])[CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH:51]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[C:53]([CH2:60][C:61](O)=[O:62])=[CH:52]1.Cl.[Cl-].[Na+]>C(Cl)Cl.O.ON1C2C=CC=CC=2N=N1>[C:45]1([C:26]2([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:34]3[CH:30]([CH2:31][N:32]([C:61](=[O:62])[CH2:60][C:53]4[C:54]5[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=5)[NH:51][CH:52]=4)[CH2:33]3)[C:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])([OH:35])[CH:28]([OH:44])[CH2:27]2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 802Indole-3-Acetic AcidHCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 677192977,7-Diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol hydrochloride

Product 1

HCID 19047655(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(3-indolylacetyl)-perhydroisoindole-4,5-diolYield 74.5%

Reagents, catalysts & solvents 2

HCID 27960291-Hydroxybenzotriazole hydrateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.46 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 0.34 cm3 of diisopropylamine are added to a solution of 0.9 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol hydrochloride, 0.4 g of 3-indolylacetic acid and 20 mg of 1-hydroxybenzotriazole hydrate in 90 cm3 of methylene chloride, cooled to 0° C. The mixture is stirred at room temperature for 15 hours, acidified with 0.1N HCl and then taken up in an aqueous saturated solution of sodium chloride. The organic phase is decanted, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The foam obtained is recrystallised in 10 cm3 of boiling acetonitrile. 0.85 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(3-indolylacetyl)-perhydroisoindole-4,5-diol is obtained in the form of a white solid which melts at 266° C.

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 foam obtained
  5. customis recrystallised in 10 cm3 of boiling acetonitrile

Sources & evidence

ORD record
ord-470ba2d6b6e74b2eaa7fd8bb1a8ad410
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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