Triethylamine → HCID 67718683, compound

HRID 2211407Notes

Reaction equation

HRID 2211407 reaction equation
C(N(CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.Cl.[C:24]([O:27][CH:28]1[CH2:36][C:35]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:34]2[CH:30]([CH2:31][NH:32][CH2:33]2)[C:29]1=[O:49])(=[O:26])[CH3:25]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:24]([O:27][CH:28]1[CH2:36][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:34]2[CH:30]([CH2:31][NH:32][CH2:33]2)[C:29]1=[O:49])(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 67718682HCID 67718682, compound

Product 1

HCID 67718683HCID 67718683, compoundYield 122.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

46.9 cm3 of triethylamine, 11.8 g of di-tert-butyl dicarbonate and then 0.3 g of 4-dimethylaminopyridine are added to a suspension of 19 g of (3aRS,5RS,7aRS)-5-acetoxy-7,7-diphenyl-perhydroisoindol-4-one hydrochloride in 200 cm3 of dry methylene chloride at a temperature of about 5° C., while stirring. The reaction mixture is stirred at room temperature for 24 hours and then washed with an aqueous saturated solution of sodium bicarbonate. The organic phase is decanted, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallised in 120 cm3 of diisopropyl ether. 21 g of (3aRS,5RS,7aRS)-5-acetoxy-7,7-diphenyl-perhydroisoindol-4-one are obtained in the form of white crystals which melt at 213° C.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 24 hours
  2. washwashed with an aqueous saturated solution of sodium bicarbonate
  3. customThe organic phase is decanted
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallised in 120 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-fdd5488f62604388aa65b6da3596ed43
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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