Triethylamine → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)-acetyl]-perhydroisoindole-4,5-diol

HRID 2211425Notes

Reaction equation

HRID 2211425 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][C:17](Cl)=[O:18].Cl.[C:21]1([C:27]2([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:35]3[CH:31]([CH2:32][NH:33][CH2:34]3)[C:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])([OH:36])[CH:29]([OH:45])[CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:46]1([C:27]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:35]3[CH:31]([CH2:32][N:33]([C:17](=[O:18])[CH2:16][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][CH3:8])[CH2:34]3)[C:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])([OH:36])[CH:29]([OH:45])[CH2:28]2)[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1795022-(2-Methoxyphenyl)acetyl chlorideHCID 677192977,7-Diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol hydrochloride

Product 1

HCID 67783659(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)-acetyl]-perhydroisoindole-4,5-diol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4.2 cm3 of triethylamine and then 2.4 g of (2-methoxyphenyl)-acetyl chloride in 50 cm3 of methylene chloride are added to a solution of 4.5 g of (3aRS, 4RS, 5RS, 7aRS )-7,7-diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol hydrochloride in 100 cm3 of methylene chloride, cooled to 0° C. The reaction mixture is stirred at room temperature for 90 minutes; it is washed with twice 10 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid which has crystallised out is taken up in 100 cm3 of diisopropyl ether and then filtered off and washed with 50 cm3 of a saturated solution of sodium bicarbonate and then 50 cm3 of diisopropyl ether. 4.35 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)-acetyl]-perhydroisoindole-4,5-diol are obtained in the form of a light beige solid which melts at 278° C.

Workup

  1. washit is washed with twice 10 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe solid which has crystallised out
  5. filtrationfiltered off
  6. washwashed with 50 cm3 of a saturated solution of sodium bicarbonate

Sources & evidence

ORD record
ord-ac91dd6ff7c24ac3b0b733877d62a032
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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