Triethylamine → HCID 56978006, compound

HRID 375438

Reaction equation

HRID 375438 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11](Cl)=[O:12])=[CH:2]1.C(N(CC)CC)C.Cl.[C:23]1([C:29]2([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@@H:37]3[C@@H:33]([CH2:34][NH:35][CH2:36]3)[C@@:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[O:45][CH3:46])([OH:38])[CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[C:47]1([C:29]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:37]3[C@@H:33]([CH2:34][N:35]([C:11](=[O:12])[C:10](=[O:14])[C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)[CH2:36]3)[C@@:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[O:45][CH3:46])([OH:38])[CH2:31][CH2:30]2)[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 899523-Indoleglyoxylyl chlorideHCID 70218598(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

Product 1

HCID 56978006HCID 56978006, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 0.43 g of 2-(3-indolyl)-2-oxoacetyl chloride in 20 cm3 of dry dichloromethane and then a solution of 0.6 cm3 of triethylamine in 5 cm3 of dry dichloromethane are added in succession to a suspension of 0.96 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride in 25 cm3 of dry dichloromethane at room temperature, while stirring. The reaction mixture is stirred at this temperature for 24 hours, subsequently diluted with 200 cm3 of dichloromethane, washed with 100 cm3 of an aqueous 1N solution of sodium hydroxide and with 50 cm3 of an aqueous saturated solution of sodium chloride, and is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2.5 cm, height 1 cm) by eluting under a pressure of 0.4 bar of nitrogen with a mixture of 1,2-dichloroethane and methanol (70/30 by volume) and collecting fractions of 15 cm3. Fractions 2 to 9 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 1.15 g of (3aS,4S,7aS)-7,7-diphenyl-2-[2-oxo-2-(3-indolyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol are obtained in the form of an orange foam.

Workup

  1. stirringThe reaction mixture is stirred at this temperature for 24 hours
  2. washwashed with 100 cm3 of an aqueous 1N solution of sodium hydroxide and with 50 cm3 of an aqueous saturated solution of sodium chloride
  3. dry with materialis dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 2.5 cm, height 1 cm)
  6. washby eluting under a pressure of 0.4 bar of nitrogen with a mixture of 1,2-dichloroethane and methanol (70/30 by volume)
  7. customcollecting fractions of 15 cm3
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-06c4dca4b5eb4defb8c1dbf6a287d814
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Linked notes

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