3,3-Diphenyl-2-pyrrolidinone → HCID 67443366, compound

HRID 1667192Notes

Reaction equation

HRID 1667192 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH3:25][C@@H:26]1[O:31][C@H:30]([CH3:32])[CH2:29][N:28]([C:33]([C:35]2[CH:36]=[C:37]([S:41](Cl)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=2)=[O:34])[CH2:27]1>O1CCCC1.CCOCC>[CH3:25][C@H:26]1[O:31][C@@H:30]([CH3:32])[CH2:29][N:28]([C:33]([C:35]2[CH:36]=[C:37]([S:41]([N:9]3[CH2:10][CH2:11][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:8]3=[O:12])(=[O:42])=[O:43])[CH:38]=[CH:39][CH:40]=2)=[O:34])[CH2:27]1

Participants

6

Reactant 3

HCID 2382533,3-Diphenyl-2-pyrrolidinoneHCID 23665647Potassium tert-butoxideHCID 86640837HCID 86640837, compound

Product 1

HCID 67443366HCID 67443366, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 3,3-diphenylpyrrolidin-2-one (166 mg, 0.7 mmol; Example 1A) in anhydrous tetrahydrofuran (6 mL) was added potassium tert-butoxide (1 mL, 1.0 M in tetrahydrofuran) at room temperature followed by stirring for 30 minutes. Then the crude 3-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)benzene-1-sulfonyl chloride (0.7 mmol; Example 147A) in tetrahydrofuran (8 mL) was added slowly. The mixture was stirred at room temperature for 3 hours. Then the mixture was concentrated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate=1:1) to give crude material. The crude material was dissolved in ether (60 mL), the insoluble solid was removed, and the ether solution was concentrated to give the titled compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90 (m, 3H), 1.10 (m, 3H), 2.83 (m, 3H), 3.30-3.60 (m, 4H), 3.80 (m, 2H), 4.37 (m, 1H), 7.00 (m, 4H), 7.20 (m, 6H), 7.71 (t, 1H, J=7 Hz), 7.88 (m, 1H), 8.00 (m, 2H); MS (ESI) m/z 519 (M+H)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. concentrationThen the mixture was concentrated
  3. customThe residue was purified by chromatography on silica gel (hexane/ethyl acetate=1:1)
  4. customto give crude material
  5. customthe insoluble solid was removed
  6. concentrationthe ether solution was concentrated

Sources & evidence

ORD record
ord-f5e8e1a63373439589d85d6699b0b63c
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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