Sulfuric Acid → (S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

HRID 3676

Reaction equation

HRID 3676 reaction equation
S(=O)(=O)(O)O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O:19]=[C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[N:21]1[C@@H:30]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:31]([N:33]1[CH:38]=[CH:37][CH2:36][CH:35]=[CH:34]1)=[O:32].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC>[O:29]=[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:19])[N:21]1[C@H:30]1[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH:34]2[CH2:35][CH2:36][CH:37]=[CH:38][N:33]2[C:31]1=[O:32]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 15380836(S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine

Product 1

HCID 9863597(S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

Combine sulfuric acid (3.0 mL, 96%) and trifluoroacetic anhydride (300 mL). Add (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine (1.0 mmol). After 30 minutes, pour the reaction mixture into a mixture of saturated aqueous sodium bicarbonate and ice. Extract with ethyl acetate and then with methylene chloride. Combine the organic layers and filter through a plug of silica gel. Rinse the silica gel with dichloromethane. Evaporate the filtrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 10% ethyl acetate/hexane and then 25% ethyl acetate/hexane to give the title compound.

Workup

  1. additionpour the reaction mixture
  2. extractionExtract with ethyl acetate
  3. filtrationfilter through a plug of silica gel
  4. washRinse the silica gel with dichloromethane
  5. customEvaporate the filtrate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-f3c835216c0344d1af2af2f75940e898
Source dataset
uspto-grants-1998_03
Patent number
US05734049

Linked notes

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