2-Pyrrolidone → HCID 70981703, compound

HRID 1475413Notes

Reaction equation

HRID 1475413 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].CC(C)([O-])C.[K+].[C:13]([O:17][C:18]([N:20]1[C:28]2[C:23](=[CH:24][C:25]([Br:31])=[C:26]([CH2:29]Br)[CH:27]=2)[C:22]([CH3:33])([CH3:32])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl-].[NH4+]>C1COCC1>[C:13]([O:17][C:18]([N:20]1[C:28]2[C:23](=[CH:24][C:25]([Br:31])=[C:26]([CH2:29][N:1]3[CH2:5][CH2:4][CH2:3][C:2]3=[O:6])[CH:27]=2)[C:22]([CH3:33])([CH3:32])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 120252-PyrrolidoneHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 86724008HCID 86724008, compound

Product 1

HCID 70981703HCID 70981703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-pyrrolidinone (0.8 g, 9.4 mmol) in THF (15.6 mL) was added potassium tert-butoxide (1.05 g, 9.4 mmol) and the mixture was stirred for 30 minutes at room temperature. 5-Bromo-6-bromomethyl-3,3-dimethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester was added in one portion and the reaction stirred for 2 h at room temperature. Saturated aqueous ammonium chloride (15 mL) was added and the mixture extracted with EtOAc. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60) gave the title compound (0.17 g) MS: [M+H]+=424.

Workup

  1. stirringthe reaction stirred for 2 h at room temperature
  2. extractionthe mixture extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washChromatography (silica gel, gradient elution, 0-100%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-d17699f33d6a4af8825617043e62925f
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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